Diisopropylethylamine → 6-Chloro-2-((S)-3-hydroxymethyl-ethyl-pyrrolidin-1-yl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide

HRID 1056722Notes

Reaction equation

HRID 1056722 reaction equation
[F:1][C:2]1([F:25])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17](Cl)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])(O)[CH2:4][CH2:3]1.[CH3:26][CH2:27]N(C(C)C)C(C)C.[OH:35][CH2:36][C@H:37]1[CH2:41][CH2:40][N:39](CC)[CH2:38]1>>[F:1][C:2]1([F:25])[CH2:7][CH2:6][CH:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([N:39]4[CH2:40][CH2:41][CH:37]([CH2:36][OH:35])[C@@H:38]4[CH2:26][CH3:27])=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 28064486[(3S)-1-ethylpyrrolidin-3-yl]methanolHCID 1185560922,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1317364336-Chloro-2-((S)-3-hydroxymethyl-ethyl-pyrrolidin-1-yl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide

Procedure

The title compound was synthesized according to the procedure described in example 1 using 2,6-dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxycyclohexylmethyl)-amide, DIPEA and (S)-3-hydroxymethyl-ethyl-pyrrolidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (1H), 7.48 (2H), 6.69 (1H), 4.72 (1H), 3.66 (m, 2H), 3.49 (m, 2H), 3.32 (m, 2H), 2.44 (m, 2H), 2.06 (m, 2H), 1.85 (m, 2H), 1.74-1.76 (m, 5H), 1.27-1.30 (m, 2H). m/z: 466 [M+H]

Sources & evidence

ORD record
ord-747d729d23f34f1bbfdad34e219a1f4e
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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