Ethanolamine → 6-Chloro-2-(2-hydroxy-ethylamino)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-amide

HRID 1056670Notes

Reaction equation

HRID 1056670 reaction equation
[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH:5]([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])[CH2:4][CH2:3]1.[NH2:25][CH2:26][CH2:27][OH:28]>>[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([NH:25][CH2:26][CH2:27][OH:28])=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 1185559652,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluorocyclohexylmethyl)-amide

Product 1

HCID 1185666086-Chloro-2-(2-hydroxy-ethylamino)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexyl methyl)-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-cyclohexylmethyl)-amide, and 2-amino-ethanol. 1H NMR (400 MHz, DMSO-d6): δ 8.70 (t, J=5.81 Hz, 1H), 7.59 (d, J=9.21 Hz, 1H), 7.47 (s, 2H), 7.27 (t, J=5.21 Hz, 1H), 6.87 (d, J=9.21 Hz, 1H), 4.79-4.81 (m, 1H), 3.55-3.59 (m, 2H), 3.44-3.48 (m, 2H), 3.22-3.23 (m, 2H), 1.98-2.03 (m, 2H), 1.73-1.85 (m, 5H), 1.22-1.31 (m, 2H). m/z: 398.3 [M+H]+

Sources & evidence

ORD record
ord-c5246bea5a104b5580f8b5366a020ddb
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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