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 2271888노트

반응식

HRID 2271888 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

(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.

후처리

  1. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-f4ead2f221e045c1bf6631344c1c1283
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120749B2

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