Phenolate → tert-butyl 4-(2-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylate

HRID 1400918ノート

反応式

HRID 1400918 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.CC([O-])(C)C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:26]3[N:27]=[CH:28][N:29]([CH2:31][CH2:32][N:33]4[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]4)[CH:30]=3)[S:25][C:18]=12.Cl.NC1C=CC(O)=C(F)C=1.C1([O-])C=CC=CC=1>CN1C(=O)CCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[CH:23]=[C:24]([C:26]4[N:27]=[CH:28][N:29]([CH2:31][CH2:32][N:33]5[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH2:38]5)[CH:30]=4)[S:25][C:18]=23)=[C:4]([F:9])[CH:3]=1

参加物

7

反応物 5

HCID 119047PhenolateHCID 2735918Phenol, 4-amino-2-fluoro-HCID 195992014-Amino-2-fluorophenol hydrochlorideHCID 23665647Potassium tert-butoxide2 回HCID 67442621tert-butyl 4-(2-(4-(7-chlorothieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylate

生成物 1

HCID 67442156tert-butyl 4-(2-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylate収率 47%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
100 °C

実験手順

To a stirred solution of 4-amino-2-fluorophenol x HCl (1.64 g, 10.05 mmol) in NMP (30 mL) was added t-BuOK (2.25 g, 20.1 mmol). After 30 min, compound 305 (3.75 g, 8.37 mmol) was added and the reaction mixture was heated at 100° C. for 1 h. A solution of 4-amino-2-fluorophenol HCl (1.64 g, 10.05 mmol) in NMP (30 mL) in a separate flask was treated with t-BuOK (2.25 g, 20.1 mmol) and the resultant phenolate solution was added to the reaction mixture at 100° C. After 30 min, the reaction was quenched by addition of water and the precipitate was collected by filtration, dried and triturated with MTBE to afford the title compound 306 (2.10 g, 3.90 mmol, 47% yield) as a beige solid. MS (m/z): 539.39 (M+H).

後処理

  1. waitAfter 30 min
  2. customthe reaction was quenched by addition of water
  3. filtrationthe precipitate was collected by filtration
  4. customdried
  5. customtriturated with MTBE

出典と根拠

ORDレコード
ord-adfe92d5b6324b769324c96a74dca69d
出典データセット
uspto-grants-2014_12
特許番号
US08906852B2

反応ノート

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