HCID 57510155, compound → HCID 57510249, compound

HRID 624218Notes

Reaction equation

HRID 624218 reaction equation
[C:1]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([N:21]3[CH2:29][C:28]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[CH2:22]3)=[O:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]>[Pd].CO>[C:1]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([N:21]3[CH2:29][C:28]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[CH2:22]3)=[O:20])=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 57510155HCID 57510155, compound

Product 1

HCID 57510249HCID 57510249, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-[4-(1-isobutyryl-1,2,3,6-tetrahydropyridin-4-yl)phenyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide (50 mg, 0.128 mmol) and methanol (10 ml) were added to 5% Pd—C, wet (10.00 mg, 0.094 mmol) in a 50 ml pressure bottle and stirred for 16 hours at 30 psi and room temperature. The mixture was filtered through a nylon membrane and concentrated. Chromatography provided the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.60 (s, 1H), 8.50 (d, J=5.0 Hz, 1H), 8.35 (s, 1H), 7.49-7.40 (m, 3H), 7.13 (m, 2H), 4.79 (m, 4H), 4.56 (m, 1H), 4.05 (m, 1H), 3.12 (m, 1H), 2.90 (m, 1H), 2.71 (m, 1H), 2.57 (m, 1H), 1.79 (m, 2H), 1.55-1.30 (m, 2H), 1.02 (m, 6H); MS (ESI(+)) m/e 393 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-23686fa8449a4e4db4ad60e79f345866
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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