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

HRID 1027796Notes

Reaction equation

HRID 1027796 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.C(#N)C.[C:37]([OH:45])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CO>[C:37]([OH:45])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=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 6342AcetonitrileHCID 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 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask was added 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate freebase (99.9 mg, 0.221 mmol, 1 eq) and acetonitrile (2.3 mL), followed by the addition of benzoic acid (33.1 mg, 0.271 mmol, 1.23 equiv). After the reaction mixture was stirred at room temperature for 30 minutes, methanol (0.5 mL) was added. The slurry was heated to 65° C. and stirred for 30 minutes, then methanol was evaporated. The reaction mixture was cooled to room temperature and stirred for 2 hours. The solid was collected by filtration, washed with MTBE (1 mL) and dried at 40-45° C. under vacuum overnight to afford 3-(4-(aminomethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate benzoate (104.1 mg, 82.1%) as an off-white solid.

Workup

  1. temperatureThe slurry was heated to 65° C.
  2. stirringstirred for 30 minutes
  3. custommethanol was evaporated
  4. temperatureThe reaction mixture was cooled to room temperature
  5. stirringstirred for 2 hours
  6. filtrationThe solid was collected by filtration
  7. washwashed with MTBE (1 mL)
  8. customdried at 40-45° C. under vacuum overnight

Sources & evidence

ORD record
ord-1fe12f4738d94561b7e548e7477c1882
Source dataset
uspto-grants-2014_05
Patent number
US08735408B2

Reaction notes

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