Hydrochloric Acid → (S)-4-(Benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochloride

HRID 2387494ノート

反応式

HRID 2387494 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@H:28]([F:31])[CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:33].C(OCC)C>C(Cl)Cl>[ClH:33].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@H:28]([F:31])[CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 25054547(S)-4-(Benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one

生成物 1

HCID 68456200(S)-4-(Benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochloride収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (S)-4-(benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (56 mg, 0.12 mmol) in CH2Cl2 (1.5 mL) was treated with anhydrous HCl in diethyl ether (0.12 mL, 0.12 mmol, 1.0 M). The reaction mixture was stirred at ambient temperature for 2 h, and then the solids were collected by filtration and dried to yield the title compound (51.4 mg, 85%) as a white powder: mp 197-200° C.; 1H NMR (500 MHz, DMSO-d6) δ 10.62-10.50 (m, 1H), 8.25 (s, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.80 (s, 1H), 7.61 (d, J=7.5 Hz, 1H), 7.48-7.42 (m, 5H), 7.39-7.36 (m, 1H), 6.13 (dd, J=7.5, 3.0 Hz, 1H), 5.99 (d, J=2.5 Hz, 1H), 5.54-5.39 (m, 1H), 5.16 (s, 2H), 4.87-4.82 (m, 2H), 3.81-3.53 (m, 4H), 3.55-3.20 (m, 2H, overlapping with H2O peak), 2.14-2.01 (s, 2H); ESI MS m/z 433 [M+H]+; HPLC (Method A)>99% (AUC), tR=14.4 min; optical rotation [α]22.5D-8.4° (c 0.095, Methanol).

後処理

  1. filtrationthe solids were collected by filtration
  2. customdried

出典と根拠

ORDレコード
ord-0175d4cb26e14a5292c5b081bc1ebee9
出典データセット
uspto-grants-2012_09
特許番号
US08268868B2

反応ノート

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