Hydrogen Bromide → HCID 57434551, compound

HRID 222984Notes

Reaction equation

HRID 222984 reaction equation
C(#N)C.[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[N:12]1[C:17]2[N:18]=[C:19]([NH:37][CH2:38][C:39]3[NH:40][CH:41]=[CH:42][N:43]=3)[N:20]=[C:21]([C:22]3[CH:23]=[C:24]([CH:33]=[CH:34][C:35]=3[CH3:36])[C:25]([NH:27][C:28]3[S:29][CH:30]=[CH:31][N:32]=3)=[O:26])[C:16]=2[CH:15]=[CH:14][C:13]1=[O:44].[BrH:45]>O>[BrH:45].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[N:12]1[C:17]2[N:18]=[C:19]([NH:37][CH2:38][C:39]3[NH:43][CH:42]=[CH:41][N:40]=3)[N:20]=[C:21]([C:22]3[CH:23]=[C:24]([CH:33]=[CH:34][C:35]=3[CH3:36])[C:25]([NH:27][C:28]3[S:29][CH:30]=[CH:31][N:32]=3)=[O:26])[C:16]=2[CH:15]=[CH:14][C:13]1=[O:44]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 6342AcetonitrileHCID 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 57434551HCID 57434551, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetonitrile (300 uL) was added to amorphous 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 from Example 79c (16.0 mg) at room temperature resulting in a mixture. Hydrobromic acid was added (1.0 equivalent; 1N in water) resulting in a clear solution. The following day, a white precipitate was observed. The product was filtered, washed with acetonitrile, and dried overnight in a vacuum oven at about 50° C. with a slow nitrogen bleed. The yield was 52.0% (9.5 mg) of title compound (melt begins at <50° C. by DSC).

Workup

  1. customat room temperature
  2. customresulting in a mixture
  3. customresulting in a clear solution
  4. filtrationThe product was filtered
  5. washwashed with acetonitrile
  6. customdried overnight in a vacuum oven at about 50° C. with a slow nitrogen

Sources & evidence

ORD record
ord-68f363373e554491b6a35f063c2f7f79
Source dataset
uspto-grants-2012_06
Patent number
US08207176B2

Reaction notes

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