Hydrochloric Acid → (4-(6-(3-Aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone hydrochloride

HRID 2271906Notes

Reaction equation

HRID 2271906 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:25]5[CH:30]=[C:29]([F:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=5)[CH:23]=4)[N:18]=[CH:17][C:16]=3[C:34]([CH:36]3[CH2:38][CH2:37]3)=[O:35])=[CH:10][CH:9]=2)[CH2:3]1.Cl>CO.C(OCC)C>[ClH:33].[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:25]5[CH:30]=[C:29]([F:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=5)[CH:23]=4)[N:18]=[CH:17][C:16]=3[C:34]([CH:36]3[CH2:38][CH2:37]3)=[O:35])=[CH:10][CH:9]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66715684(4-(6-(3-Aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxy phenyl)quinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66716241(4-(6-(3-Aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone hydrochlorideYield 175.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(4-(6-(3-aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone (12 mg, 0.02 mmol) was suspended in methanol (1 mL) at 0° C. followed by dropwise addition of HCl in diethyl ether (2 M) until complete dissolution of the solid was observed. The solvent was removed under reduced pressure to afford the desired product (10 mg, 80%) as an orange-red solid: 1H NMR (500 MHz, MeOD) δ 9.39 (s, 1H), 8.27-8.19 (m, 2H), 8.13 (br s, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.72 (dd, J=9.2, 2.7 Hz, 1H), 7.21-7.07 (m, 3H), 4.52 (d, J=10.8 Hz, 1H), 4.06-3.98 (m, 1H), 3.43-3.31 (m, 3H), 2.90-2.81 (m, 1H), 2.28-2.16 (m, 1H), 2.01-1.92 (m, 1H), 1.80-1.68 (m, 2H), 1.31-1.15 (m, 4H). ESI MS m/z 532 [C29H27ClFN5O2+H]+; HPLC 98.7% (AUC), tR=10.82 min.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0c9c213d81bb48bb9bbbbe3542bd475e
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…