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4-Methylmorpholine → Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylcarbamate

HRID 2361338
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HRID 2361338 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([F:39])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:36](O)=[O:37])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].F[P-](F)(F)(F)(F)F.[N:49]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.CN1CCOCC1>CN(C=O)C.O>[C:36]([C:21]1[C:22]2[NH:23][C:24]3[C:29]([C:30]=2[C:18]([C:14]2[C:13]([F:39])=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:17]=[CH:16][CH:15]=2)=[CH:19][N:20]=1)=[CH:28][CH:27]=[C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])[CH:25]=3)(=[O:37])[NH2:49]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 679948974-(3-(Benzyloxycarbonylamino)-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid

생성물 1

HCID 67994974
Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylcarbamate
수율 90.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A burgundy, homogeneous solution of 4-(3-(benzyloxycarbonylamino)-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.7 g, 1.322 mmol), ammonium chloride (0.283 g, 5.29 mmol), BOP (0.760 g, 1.719 mmol), DIPEA (1.108 mL, 6.35 mmol) and N-methylmorpholine (0.567 mL, 5.16 mmol) in DMF (8 mL) under nitrogen was stirred. After 2 hr, water (20 mL) was added, and the reaction was stirred at room temperature for 45 min. The precipitate was collected, rinsed with water and dried over Drierite under vacuum to give the desired product (0.6318 g, 1.195 mmol, 90% yield) as a tan solid.

후처리

  1. customThe precipitate was collected
  2. washrinsed with water
  3. dry with materialdried over Drierite under vacuum

출처 및 근거

ORD 기록
ord-f87961b347f54b8aaf94a6a7ddb230d8
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08685969B2

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