3-Methoxy-1-propanol → 6-Chloro-2-(3-methoxy-propoxy)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexyl methyl)-amide

HRID 1056674Notes

Reaction equation

HRID 1056674 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])([OH:8])[CH2:4][CH2:3]1.[CH3:26][O:27][CH2:28][CH2:29][CH2:30][OH:31]>>[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]([O:31][CH2:30][CH2:29][CH2:28][O:27][CH3:26])=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 741163-Methoxy-1-propanolHCID 1185560922,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1185665886-Chloro-2-(3-methoxy-propoxy)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexyl methyl)-amide

Procedure

The title compound was synthesized according to the procedure described in example 9 using 2,6-dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide and 3-methoxy-propan-1-ol. 1H NMR (400 MHz, DMSO-d6): δ 8.74 (t, J=6.01 Hz, 1H), 8.03 (d, J=9.61 Hz, 1H), 7.77-7.80 (m, 1H), 7.69-7.71 (m, 1H), 7.10 (d, J=9.21 Hz, 1H), 4.68 (s, 1H), 4.45 (t, J=6.41 Hz, 2H), 3.47-3.50 (m, 2H), 3.38-3.39 (m, 2H), 3.25 (s, 3H), 2.01-2.04 (m, 4H), 1.90-2.00 (m, 2H), 1.67-1.72 (m, 4H). m/z: 443.2 [M+H]+

Sources & evidence

ORD record
ord-3ae4c484c0e3434a94f00b7c1f81c54e
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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