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

HRID 2271908노트

반응식

HRID 2271908 반응식
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([Cl:32])[CH:25]=5)[CH:22]=4)[N:17]=[CH:16][C:15]=3[C:33]([CH:35]3[CH2:37][CH2:36]3)=[O:34])=[CH:9][CH:8]=2)[CH2:3]1.Cl>CO.C(OCC)C>[ClH:32].[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([Cl:32])[CH:25]=5)[CH:22]=4)[N:17]=[CH:16][C:15]=3[C:33]([CH:35]3[CH2:36][CH2:37]3)=[O:34])=[CH:9][CH:8]=2)[CH2:3]1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 66716234(4-(6-(3-Aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone

생성물 1

HCID 66716423(4-(6-(3-Aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone hydrochloride수율 276.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

(4-(6-(3-aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone (15 mg, 0.03 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 (23 mg, quant.) as a yellow-brown solid. 1H NMR (500 MHz, MeOD) δ 9.39 (s, 1H), 8.28-8.19 (m, 2H), 8.16 (br s, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.79 (dd, J=9.1, 2.7 Hz, 1H), 7.26-7.16 (m, 2H), 6.94 (d, J=9.2 Hz, 1H), 4.16-4.08 (m, 1H), 4.05-3.97 (m, 1H), 3.88-3.79 (m, 1H), 3.78-3.69 (m, 2H), 2.85 (br s, 1H), 2.64-2.53 (m, 1H), 2.34-2.21 (m, 1H), 1.25-1.15 (m, 4H). ESI MS m/z 518 [C28H25ClFN5O2+H]+; HPLC 98.1% (AUC), tR=5.13 min.

후처리

  1. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-05552504360c41208696e4b2d4521138
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120749B2

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