Acetone → 3-{8-(2,6-difluorophenyl)-2-[(1H-imidazol-2-ylmethyl)amino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl}-4-methyl-N-1,3-thiazol-2-ylbenzamide benzenesulfonate

HRID 222986Notes

Reaction equation

HRID 222986 reaction equation
CC(C)=O.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[N:13]1[C:18]2[N:19]=[C:20]([NH:38][CH2:39][C:40]3[NH:41][CH:42]=[CH:43][N:44]=3)[N:21]=[C:22]([C:23]3[CH:24]=[C:25]([CH:34]=[CH:35][C:36]=3[CH3:37])[C:26]([NH:28][C:29]3[S:30][CH:31]=[CH:32][N:33]=3)=[O:27])[C:17]=2[CH:16]=[CH:15][C:14]1=[O:45].[C:46]1([S:52]([OH:55])(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>O>[C:46]1([S:52]([OH:55])(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[N:13]1[C:18]2[N:19]=[C:20]([NH:38][CH2:39][C:40]3[NH:44][CH:43]=[CH:42][N:41]=3)[N:21]=[C:22]([C:23]3[CH:24]=[C:25]([CH:34]=[CH:35][C:36]=3[CH3:37])[C:26]([NH:28][C:29]3[S:30][CH:31]=[CH:32][N:33]=3)=[O:27])[C:17]=2[CH:16]=[CH:15][C:14]1=[O:45]

Participants

5

Reactant 3

HCID 180AcetoneHCID 7371Benzenesulfonic AcidHCID 119481803-{8-(2,6-difluorophenyl)-2-[(1H-imidazol-2-ylmethyl)amino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl}-4-methyl-N-1,3-thiazol-2-ylbenzamide

Product 1

HCID 866085713-{8-(2,6-difluorophenyl)-2-[(1H-imidazol-2-ylmethyl)amino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl}-4-methyl-N-1,3-thiazol-2-ylbenzamide benzenesulfonateYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Acetone (200 uL) was added to free-base version of 3-{8-(2,6-difluorophenyl)-2-[(1H-imidazol-2-ylmethyl)amino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl}-4-methyl-N-1,3-thiazol-2-ylbenzamide (10.4 mg), and the resulting mixture was heated to 50° C. Benzenesulfonic acid was added (1.0 equivalent; 1N in water) resulting in a clear solution. The mixture was cooled to room temperature and shook overnight. The product was filtered, washed with acetone, and dried for several hours in a vacuum oven at 50° C. with a slow nitrogen bleed. The yield was 83.2% (5.8 mg) of title compound with a melting onset at 317° C. (determined by DSC).

Workup

  1. customresulting in a clear solution
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe product was filtered
  4. washwashed with acetone
  5. customdried for several hours in a vacuum oven at 50° C. with a slow nitrogen

Sources & evidence

ORD record
ord-ef5e40ab6e974148a6a7699784453312
Source dataset
uspto-grants-2012_06
Patent number
US08207176B2

Reaction notes

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