Pyrrolidine → 6-Chloro-2-pyrrolidin-1-yl-quinoline-5-carboxylic acid ((1S,3S)-1-hydroxy-3-methyl-cyclohexylmethyl)-amide

HRID 1056705Notes

Reaction equation

HRID 1056705 reaction equation
[OH:1][C@@:2]1([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])[CH2:7][CH2:6][CH2:5][C@H:4]([CH3:8])[CH2:3]1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[OH:1][C@@:2]1([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:7][CH2:6][CH2:5][C@H:4]([CH3:8])[CH2:3]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 866233642,6-Dichloro-N-{[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl}quinoline-5-carboxamide

Product 1

HCID 1185665456-Chloro-2-pyrrolidin-1-yl-quinoline-5-carboxylic acid ((1S,3S)-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 ((1S,3S)-1-hydroxy-3-methyl-cyclohexyl methyl)-amide and pyrrolidine. 1H NMR (400 MHz, DMSO-d6): δ 8.50 (t, J=6.01 Hz, 1H), 7.80 (d, J=9.22 Hz, 1H), 7.47-7.54 (m, 2H), 6.96 (d, J=9.21 Hz, 1H), 4.16 (s, 1H), 3.51-3.53 (m, 4H), 3.26-3.28 (m, 2H), 1.97-1.98 (m, 4H), 1.71-1.73 (m, 1H), 1.45-1.61 (m, 6H), 1.00-1.07 (m, 1H), 0.83-0.84 (m, 3H), 0.73-0.79 (m, 1H). m/z: 402.2 [M+H]+

Sources & evidence

ORD record
ord-22b19dc7c5f14f95ad4c99ab1b745964
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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