HCID 57510602, compound → HCID 57511049, compound

HRID 624280Notes

Reaction equation

HRID 624280 reaction equation
[CH3:1][CH:2]([CH3:30])[C:3]([NH:5][CH:6]1[CH2:11][CH2:10][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)=[CH:8][CH2:7]1)=[O:4]>CO>[CH3:1][CH:2]([CH3:30])[C:3]([NH:5][C@@H:6]1[CH2:11][CH2:10][C: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)=[CH:8][CH2:7]1)=[O:4]

Participants

3

Reactant 1

HCID 57510602HCID 57510602, compound

Product 1

HCID 57511049HCID 57511049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A racemic mixture of N-(4-{4-[(2-methylpropanoyl)amino]cyclohex-1-en-1-yl}phenyl)-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide (250 mg) was dissolved in methanol and separated using SCF-LC with a ChiralPak AD-H 21×250 mm column to provide N-(4-{(4R)-4-[(2-methylpropanoyl)amino]cyclohex-1-en-1-yl}phenyl)-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ 8.61 (s, 1H), 8.50 (d, J=5.0 Hz, 1H), 8.41 (s, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.56-7.48 (m, 2H), 7.43 (d, J=5.1 Hz, 1H), 7.37-7.29 (m, 2H), 6.02 (bs, 1H), 4.84-4.77 (m, 4H), 3.89-3.73 (m, 1H), 2.44 (ddd, J=12.7, 8.7, 4.6 Hz, 2H), 2.41-2.26 (m, 2H), 2.14-1.97 (m, 1H), 1.93-1.81 (m, 1H), 1.67-1.49 (m, 1H), 1.00 (dd, J=6.8, 2.4 Hz, 6H); MS (ESI(+)) m/e 405 (M+H)+.

Workup

  1. customseparated

Sources & evidence

ORD record
ord-4095f1931fa44e17bad52eac845ad912
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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