Pyrrolidine → 6-Chloro-2-(3-pyrrolidin-1-yl-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluorocyclo hexyl methyl)-amide

HRID 1056790Notes

Reaction equation

HRID 1056790 reaction equation
[F:1][C:2]1([F:29])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([CH:23]4[CH2:27][CH2:26][C:25](=O)[CH2:24]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[F:1][C:2]1([F:29])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([CH:23]4[CH2:27][CH2:26][CH:25]([N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[CH2:24]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 1185696266-Chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide

Product 1

HCID 1185666876-Chloro-2-(3-pyrrolidin-1-yl-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluorocyclo hexyl methyl)-amide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was synthesized according to the procedure described in example 133 using 6-chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide, pyrrolidine, glacial acetic acid and sodium triacetoxyborohydride. 1H NMR (400 MHz, DMSO-d6): δ 8.80 (t, J=5.82 Hz, 1H), 8.01-7.95 (m, 2H), 7.76-7.74 (m, 1H), 7.61-7.56 (m, 1H), 3.55-3.44 (m, 1H), 3.43-3.41 (m, 1H), 3.27 (t, J=6.2 Hz, 2H), 2.74-2.66 (m, 1H), 2.64-2.50 (m, 1H), 2.27-2.24 (m, 1H), 2.10-1.99 (m, 5H), 1.89-1.76 (m, 6H), 1.75-1.68 (m, 2H), 1.33-1.29 (m, 5H), 1.27-1.24 (m, 2H). m/z: 476.2 [M+H]+

Sources & evidence

ORD record
ord-d4674f4c5eb54d1abcfd378df101cc51
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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