Sodium borohydride → 6-Chloro-2-(3-hydroxy-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide

HRID 1056797Notes

Reaction equation

HRID 1056797 reaction equation
[F:1][C:2]1([F:30])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([CH:24]4[CH2:28][CH2:27][C:26](=[O:29])[CH2:25]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])(O)[CH2:4][CH2:3]1.[BH4-].[Na+]>>[F:30][C:2]1([F:1])[CH2:7][CH2:6][CH:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([CH:24]4[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 1185666266-Chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1185666256-Chloro-2-(3-hydroxy-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide

Procedure

The title compound was synthesized according to the procedure described in example 136 using 6-chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxycyclohexyl methyl)-amide and NaBH4. 1H NMR (400 MHz, DMSO-d6): δ 88.72-8.76 (bs, 1H), 8.05-8.10 (m, 1H), 7.94 (d, J=9.51 Hz, 1H), 7.72-7.76 (m, 1H), 7.54-7.63 (m, 1H), 4.68 (s, 2H), 4.25-4.26 (m, 1H), 3.31-3.40 (m, 3H), 2.48-2.50 (m, 1H), 1.95-2.32 (m, 4H), 1.81-1.92 (m, 3H), 1.72-1.79 (m, 2H), 1.63-1.71 (m, 5H). m/z: 439.2 [M+H]+

Sources & evidence

ORD record
ord-b3f17abb71234a97a36ace8da31a1c9e
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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