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molecular formula C8H19N B1584993 Di-tert-butylamine CAS No. 21981-37-3

Di-tert-butylamine

Cat. No. B1584993
M. Wt: 129.24 g/mol
InChI Key: CATWEXRJGNBIJD-UHFFFAOYSA-N
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Patent
US09115124B1

Procedure details

In a reaction flask 283.5 ml dimethylsulfoxide, 29.83 g 1-(2-hydroxyethyl)piperazine (0.229 mol), 12.08 g sodium carbonate (0.144 mol), 56.70 g ter-butyl-6-chloro-2-methylpyrimidin-4-yl-(5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl)carbamate (0.114 mol) were charged at a temperature of about 25° C. and the reaction mixture was kept under these conditions for about five hours. At the end of the reaction, 760 ml water were added, the mixture was kept under stirring for about 30 minutes and the formed solid was filtered, washed with water (4×260 ml) and suspended in 440 ml methanol. 42.88 g di-terbutylamine (DBTA, 0.120 mol) were added, the temperature was brought to the solvent reflux value and 15.19 g tromethamol (TRIZMA) (0.125 mol) were added. The temperature was brought to about 25° C. and the formed solid was filtered, washed with methanol (2×45 ml) and dried in oven under vacuum at a temperature of about 50° C. for eight hours to give 44.51 g dasatinib.
Quantity
42.88 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
760 mL
Type
solvent
Reaction Step Three
Quantity
29.83 g
Type
reactant
Reaction Step Four
Quantity
12.08 g
Type
reactant
Reaction Step Four
Name
ter-butyl-6-chloro-2-methylpyrimidin-4-yl-(5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl)carbamate
Quantity
56.7 g
Type
reactant
Reaction Step Four
Quantity
283.5 mL
Type
solvent
Reaction Step Four

Identifiers

REACTION_CXSMILES
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(=O)([O-])[O-].[Na+].[Na+].C(OC(=O)[N:22]([C:39]1[CH:44]=[C:43](Cl)[N:42]=[C:41]([CH3:46])[N:40]=1)[C:23]1[S:24][C:25]([C:28](=[O:38])[NH:29][C:30]2[C:35]([CH3:36])=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:37])=[CH:26][N:27]=1)(C)(C)C.C(NC(C)(C)C)(C)(C)C.C(O)C(N)(CO)CO>O.CS(C)=O>[CH3:36][C:35]1[C:30]([NH:29][C:28]([C:25]2[S:24][C:23]([NH:22][C:39]3[CH:44]=[C:43]([N:7]4[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]4)[N:42]=[C:41]([CH3:46])[N:40]=3)=[N:27][CH:26]=2)=[O:38])=[C:31]([Cl:37])[CH:32]=[CH:33][CH:34]=1 |f:1.2.3|

Inputs

Step One
Name
Quantity
42.88 g
Type
reactant
Smiles
C(C)(C)(C)NC(C)(C)C
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(CO)(CO)N)O
Step Three
Name
Quantity
760 mL
Type
solvent
Smiles
O
Step Four
Name
Quantity
29.83 g
Type
reactant
Smiles
OCCN1CCNCC1
Name
Quantity
12.08 g
Type
reactant
Smiles
C([O-])([O-])=O.[Na+].[Na+]
Name
ter-butyl-6-chloro-2-methylpyrimidin-4-yl-(5-(2-chloro-6-methylphenylcarbamoyl)thiazol-2-yl)carbamate
Quantity
56.7 g
Type
reactant
Smiles
C(C)(C)(C)OC(N(C=1SC(=CN1)C(NC1=C(C=CC=C1C)Cl)=O)C1=NC(=NC(=C1)Cl)C)=O
Name
Quantity
283.5 mL
Type
solvent
Smiles
CS(=O)C

Conditions

Stirring
Type
CUSTOM
Details
under stirring for about 30 minutes
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
were added
FILTRATION
Type
FILTRATION
Details
the formed solid was filtered
WASH
Type
WASH
Details
washed with water (4×260 ml)
ADDITION
Type
ADDITION
Details
were added
CUSTOM
Type
CUSTOM
Details
was brought to about 25° C.
FILTRATION
Type
FILTRATION
Details
the formed solid was filtered
WASH
Type
WASH
Details
washed with methanol (2×45 ml)
CUSTOM
Type
CUSTOM
Details
dried in oven under vacuum at a temperature of about 50° C. for eight hours
Duration
8 h

Outcomes

Product
Details
Reaction Time
5 h
Name
Type
product
Smiles
CC1=CC=CC(=C1NC(=O)C2=CN=C(S2)NC=3C=C(N=C(N3)C)N4CCN(CC4)CCO)Cl
Measurements
Type Value Analysis
AMOUNT: MASS 44.51 g
YIELD: CALCULATEDPERCENTYIELD 80%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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