Benzoic Acid → 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate benzoate

HRID 1027797Notes

Reaction equation

HRID 1027797 reaction equation
[CH3:1][N:2]([CH3:33])[C:3](=[O:32])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:30][NH2:31])[CH2:19][CH2:18][N:17]([C:20]3[C:21]4[C:28]([CH3:29])=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1.CO.[C:36]([OH:44])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(#N)C>[C:36]([OH:44])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[CH3:33][N:2]([CH3:1])[C:3](=[O:32])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:30][NH2:31])[CH2:15][CH2:16][N:17]([C:20]3[C:21]4[C:28]([CH3:29])=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:18][CH2:19]2)=[O:13])[CH:6]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 887MethanolHCID 56962369Lx-7101

Product 1

HCID 573312013-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate benzoateYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reactor was charged with 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate freebase (101.1 mg, 0.224 mmol, 1 eq) and MeOH (1 mL). To the clear solution was added benzoic acid (33.9 mg, 0.278 mmol, 1.24 eq) and the resulting mixture was stirred at room temperature for 5 min to give a slurry. Acetonitrile (2 mL) was added and the slurry was heated to 70-73° C. and stirred for 5 minutes to give a solution. After being cooled to room temperature, the reaction mixture was stirred for 2 hours. The precipitate was collected by filtration and the cake was washed with MTBE (1 mL) and dried at 40-45° C. under vacuum overnight to provide the 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate benzoate (94.8 mg, 75%) as an off-white solid

Workup

  1. customto give a slurry
  2. temperaturethe slurry was heated to 70-73° C.
  3. stirringstirred for 5 minutes
  4. customto give a solution
  5. temperatureAfter being cooled to room temperature
  6. stirringthe reaction mixture was stirred for 2 hours
  7. filtrationThe precipitate was collected by filtration
  8. washthe cake was washed with MTBE (1 mL)
  9. customdried at 40-45° C. under vacuum overnight

Sources & evidence

ORD record
ord-ce3edf3785d847bcaa955dcdb37a4547
Source dataset
uspto-grants-2014_05
Patent number
US08735408B2

Reaction notes

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