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 2271908ノート

反応式

HRID 2271908 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

(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.

後処理

  1. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-05552504360c41208696e4b2d4521138
出典データセット
uspto-grants-2015_09
特許番号
US09120749B2

反応ノート

読み込み中…