Sodium Iodide → 3-(4-Fluorobenzoyl)-1,1-dimethyl-8-(2-morpholin-4-YL-ethoxy)-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester

HRID 736092

反応式

HRID 736092 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][C:19]=3[C:11]=2[C:10]([CH3:22])([CH3:21])[CH2:9][N:8]([C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:7]=1)=[O:5])[CH3:2].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[C:16]([O:20][CH2:41][CH2:42][N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)[CH:17]=[CH:18][C:19]=3[C:11]=2[C:10]([CH3:22])([CH3:21])[CH2:9][N:8]([C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:7]=1)=[O:5])[CH3:2]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 666409793-(4-Fluorobenzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester

生成物 1

HCID 574679553-(4-Fluorobenzoyl)-1,1-dimethyl-8-(2-morpholin-4-YL-ethoxy)-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester収率 10.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
75 °C

実験手順

A mixture of 3-(4-fluorobenzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (85 mg, 0.2 mmol), sodium iodide (30 mg), potassium carbonate (140 mg, 1.01 mmol) and 4-(2-chloroethyl)morpholine (free base, 300 mg, 2 mmol) and acetone (8 mL) was heated at 75° C. for 24 hours. The solid was filtered off, and the filtrate was concentrated in vacuo, and the crude product was purified by reverse-phase preparative HPLC to give the title compound (11 mg); 1H-NMR (CDCl3): δ 10.51 (1H, s), 7.72 (1H, s), 7.67 (1H, d), 7.66-7.59 (2H, m), 7.15-7.10 (2H, m), 6.86 (1H, d), 6.76 (1H, dd), 4.27-4.17 (4H, m), 4.08 (2H, brs), 3.77 (4H, m), 2.88 (2H, brs), 2.65 (4H, brs), 1.59 (6H, s), 1.25 (3H, t); MS (ES): 536 (MH+).

後処理

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe crude product was purified by reverse-phase preparative HPLC

出典と根拠

ORDレコード
ord-5d672d2a87e44a44be68f0c074832436
出典データセット
uspto-grants-2009_09
特許番号
US07595311B2

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