Diisopropylethylamine → 6-Chloro-2-(3-diethylamino-pyrrolidin-1-yl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-3-methyl-cyclohexylmethyl)-amide

HRID 1056751Notes

Reaction equation

HRID 1056751 reaction equation
[F:1][C:2]1([F:26])[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])([OH:8])[CH2:4][CH:3]1[CH3:25].CCN(C(C)C)C(C)C.[CH2:36]([N:38]([CH2:44][CH3:45])[CH:39]1[CH2:43][CH2:42][NH:41][CH2:40]1)[CH3:37]>>[F:1][C:2]1([F:26])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([N:41]4[CH2:42][CH2:43][CH:39]([N:38]([CH2:44][CH3:45])[CH2:36][CH3:37])[CH2:40]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:4][CH:3]1[CH3:25]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 199619953-(Diethylamino)pyrrolidineHCID 1185667002,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-3-methyl-cyclohexylmethyl)-amide

Product 1

HCID 1185666586-Chloro-2-(3-diethylamino-pyrrolidin-1-yl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-3-methyl-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-hydroxy-3-methyl-cyclohexylmethyl)-amide, DIPEA and 3-diethylamino-pyrrolidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.75 (1H), 7.85 (m, 1H), 7.58 (2H), 7.05 (1H), 5.43-5.56 (1H), 4.66 (s, 1H), 3.89 (m, 2H), 3.70 (m, 1H), 3.55 (m, 1H), 3.26 (m, 2H), 2.19 (m, 3H), 2.06 (m, 2H), 1.85 (m, 3H), 1.74-1.56 (m, 1H), 1.27-1.32 (m, 1H), 1.00 (m, 9H). m/z: 505 [M+H]

Sources & evidence

ORD record
ord-c9f2cd04275a4f4a914aecb954035ed1
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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