beta-Alanine, ethyl ester, hydrochloride → 3-{6-Chloro-5-[(4,4-difluoro-cyclohexylmethyl)-carbamoyl]-quinolin-2-ylamino}-propionic acid ethyl ester

HRID 1056666Notes

Reaction equation

HRID 1056666 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.Cl.[CH2:26]([O:28][C:29](=[O:33])[CH2:30][CH2:31][NH2:32])[CH3:27]>CS(C)=O>[CH2:26]([O:28][C:29](=[O:33])[CH2:30][CH2:31][NH:32][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:22])[C:12]=2[C:10](=[O:11])[NH:9][CH2:8][CH:5]2[CH2:6][CH2:7][C:2]([F:24])([F:1])[CH2:3][CH2:4]2)[N:17]=1)[CH3:27]

Participants

4

Reactant 2

HCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 1185559652,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluorocyclohexylmethyl)-amide

Product 1

HCID 1185559683-{6-Chloro-5-[(4,4-difluoro-cyclohexylmethyl)-carbamoyl]-quinolin-2-ylamino}-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was synthesized according to the procedure described in example 1 by heating 2,6-dichloro-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide, DIEPA and 3-Amino-propionic acid ethyl ester hydrochloride in DMSO at 140° C. 1H NMR (400 MHz, DMSO-d6) δ 4.16 (s, 1H), 4.00 (t, J=13.2 Hz, 2H), 3.78 (t, J=7.60 Hz, 2H), 3.28 (d, J=6.04 Hz, 2H), 8.81 (s, 1H), 7.68-7.77 (m, 2H), 6.93-7.02 (m, 1H), 4.05-4.10 (m, 2H), 3.68-3.80 (m, 2H), 3.23 (t, J=6.03 Hz, 2H), 2.01-2.03 (m, 2H), 1.73-1.88 (m, 5H), 1.22-2.27 (m, 2H), 1.15-1.19 (m, 3H). m/z: 454.0 [M+H]+

Sources & evidence

ORD record
ord-6fc872e11b9044e5b825f7d0b2c2b469
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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