Acetonitrile--water (1/1) → HCID 67045460, compound

HRID 1923895Notes

Reaction equation

HRID 1923895 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:20]([CH:21]=[CH2:22])=[CH:19][N:18]=[C:17]3[N:23]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:24]=[C:25]([NH:26][C:27]([CH:29]4[CH2:31][CH2:30]4)=[O:28])[C:16]=23)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC#N.O>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:20]([CH2:21][CH3:22])=[CH:19][N:18]=[C:17]3[N:23]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH:24]=[C:25]([NH:26][C:27]([CH:29]4[CH2:31][CH2:30]4)=[O:28])[C:16]=23)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 67045148HCID 67045148, compound

Product 1

HCID 67045460HCID 67045460, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (65 mg, 0.061 mmol) was added to a solution of (R)-tert-butyl 4-(3-(tert-butoxycarbonylamino)piperidin-1-yl)-3-(cyclopropanecarboxamido)-5-vinyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (64 mg, 0.12 mmol) in ethanol (6 mL). The mixture was stirred under a hydrogen atmosphere (balloon) for 3.5 hours. The mixture was filtered through a pad of Celite® and washed with methanol, and the filtrate evaporated in vacuo. The residue was purified by reverse phase chromatography (Biotage SP4, C-18 25M+, 15-80% CH3CN/water, 25 CV) to give (R)-tert-butyl 4-(3-(tert-butoxycarbonylamino)piperidin-1-yl)-3-(cyclopropane-carboxamido)-5-ethyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (29.4 mg, 46% yield) as a solid. LCMS (APCI+) m/z 528 (M+H)+, Retention time=4.37 minutes.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washwashed with methanol
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was purified by reverse phase chromatography (Biotage SP4

Sources & evidence

ORD record
ord-6b170c86fb5449a6babd2558fe9bb488
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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