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 1400918노트

반응식

HRID 1400918 반응식
[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

참가 물질

7

반응물 5

HCID 119047PhenolateHCID 2735918Phenol, 4-amino-2-fluoro-HCID 195992014-Amino-2-fluorophenol hydrochlorideHCID 23665647Potassium tert-butoxide2회HCID 67442621tert-butyl 4-(2-(4-(7-chlorothieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylate

생성물 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-carboxylate수율 47%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매2회

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-adfe92d5b6324b769324c96a74dca69d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906852B2

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