Sodium Hydroxide → HCID 118556059, compound

HRID 1056776Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([Cl:34])[C:18]=3[C:22](=[O:33])[NH:23][CH2:24][CH:25]3[CH2:30][CH2:29][C:28]([F:32])([F:31])[CH2:27][CH2:26]3)[N:13]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+]>>[Cl:34][C:17]1[C:18]([C:22](=[O:33])[NH:23][CH2:24][CH:25]2[CH2:30][CH2:29][C:28]([F:32])([F:31])[CH2:27][CH2:26]2)=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1)[CH:21]=[CH:20]2

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 118556062HCID 118556062, compound

Product 1

HCID 118556059HCID 118556059, compound

Procedure

1-{6-Chloro-5-[(4,4-difluoro-cyclohexylmethyl)-carbamoyl]-quinolin-2-yl}-piperidine-3-carboxylic acid ethyl ester was hydrolysed to the desired product with 2.5 M aqueous sodium hydroxide. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.41 (s, 1H), 8.72-8.75 (m, 1H), 7.73 (d, J=9.41 Hz, 1H), 7.50-7.56 (m, 2H), 7.35 (d, J=9.51 Hz, 1H), 4.48-4.51 (m, 1H), 4.18-4.21 (m, 1H), 3.15-3.25 (m, 4H), 2.48-2.52 (m, 1H), 1.97-2.03 (m, 3H), 1.82-1.85 (m, 3H), 1.63-1.76 (m, 4H), 1.45-1.51 (m, 1H), 1.27-1.31 (m, 2H). m/z: 466.3 [M+H]+

Sources & evidence

ORD record: ord-203cb8eed2264879a141338d34407d61
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399623B2

Reaction notes

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