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Triethylamine → HCID 69411964, 화합물

HRID 1294083
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HRID 1294083 반응식
[NH2:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]4[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=4[F:32])=[O:20])=[CH:14][CH:13]=3)=[CH:10][C:4]=2[N:3]=1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>CN(C=O)C.C(Cl)(Cl)Cl>[F:32][C:23]1[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:29])[F:30])=[CH:27][C:22]=1[NH:21][C:19]([NH:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]([S:41]([CH3:40])(=[O:43])=[O:42])[CH:2]([NH2:1])[NH:3][C:4]=3[CH:10]=2)=[CH:17][CH:16]=1)=[O:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178508201HCID 178508201, 화합물2회

생성물 1

HCID 69411964HCID 69411964, 화합물수율 11%

시약·촉매·용매 1

HCID 21754633chloroform N,N-dimethylformamide용매

실험 절차

To a mixture of 2-amino-5-(4-((2-fluoro-5-(trifluoromethyl)phenyl)aminocarbonylamino)phenoxy)-1H-benzimidazole (90 mg, 0.20 mmol) (prepared according to similar procedures as described for Intermediates 4, 5, and 6 and Example 22) and triethylamine (30 mg, 0.30 mmol) in DMF/CHCl3 (3 ml/1 ml) was added methanesulfonyl chloride (30 mg, 0.26 mmol). After stirring for 3 h at rt, the reaction mixture was washed with water and extracted with CHCl3. The organic layer was dried over MgSO4 and evaporated. The crude material was purified with silica gel column chromatography (AcOEt) to give the product of Example 23 (11.0 mg, 11%) and the title compound (34 mg, 25%): 1H NMR (DMSO-d6) δ 9.14 (s, 1H), 8.85 (s, 1H), 8.62 (d, 1H), 7.51 (d, 1H), 7.47 (d, 1H), 7.46 (d, 2H), 7.38 (m, 1H), 7.02 (brs, 2H), 6.97 (d, 2H), 6.82 (d, 1H), 6.70 (dd, 1H), 3.49 (s, 3H); MS m/e 524 (M+1).

후처리

  1. washthe reaction mixture was washed with water
  2. extractionextracted with CHCl3
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe crude material was purified with silica gel column chromatography (AcOEt)

출처 및 근거

ORD 기록
ord-ffbb129e0df64668b67bd5eb06dde1c3
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07238813B2

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