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

HRID 1056702Notes

Reaction equation

HRID 1056702 reaction equation
[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16](Cl)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:3]1.CCN(C(C)C)C(C)C.Cl.Cl.[N:36]1([CH:41]2[CH2:45][CH2:44][NH:43][CH2:42]2)[CH2:40][CH2:39][CH2:38][CH2:37]1>>[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([N:43]4[CH2:44][CH2:45][CH:41]([N:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)[CH2:42]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:3]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 534091671-(3-Pyrrolidinyl)-pyrrolidine 2HClHCID 1185560912,6-Dichloro-quinoline-5-carboxylic acid (3,3-difluoro-cyclohexylmethyl)-amide

Product 1

HCID 1185665756-Chloro-2-(3-pyrrolidinyl-pyrrolidin-1-yl)-quinoline-5-carboxylic acid (3,3-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 (3,3-difluoro-cyclohexylmethyl)-amide, DIPEA and 3-pyrrolidinyl-pyrrolidine dihydrochloride. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (1H), 7.48 (2H), 6.69 (1H), 3.89 (m, 1H), 3.70 (m, 1H), 3.45 (m, 1H), 3.26 (m, 2H), 2.85 (m, 1H), 2.54 (m, 4H), 2.15 (m, 1H), 2.06 (m, 2H), 1.85 (m, 3H), 1.74-1.76 (m, 5H), 1.27-1.32 (m, 2H). m/z: 478 [M+H]

Sources & evidence

ORD record
ord-8d2520f32e93437683058f2ffe0c4c03
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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