Potassium Carbonate → 2,6-Difluoro-N-(4-(oxazol-5-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide

HRID 1255139노트

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HRID 1255139 반응식
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10]([CH:12]=[O:13])[N:11]=1)=[O:5].S([CH2:39][N+:40]#[C-:41])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)=[C:10]([C:12]2[O:13][CH:41]=[N:40][CH:39]=2)[N:11]=1)=[O:5]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 24765490HCID 24765490, 화합물

생성물 1

HCID 247655822,6-Difluoro-N-(4-(oxazol-5-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide수율 72.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

Into a solution of Compound 67 (62 mg, 0.15 mmol) in 5 mL of dry methanol was added tosylmethyl isocyanide (35 mg, 0.18 mmol), followed by dry potassium carbonate (25 mg, 0.18 mmol). The reaction mixture was heated to 65° C. for 2 hours. The reaction mixture was dissolved in ethyl acetate, washed each with water and brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (eluted with 10-50% ethyl acetate in hexanes) to give Compound 76 (49 mg, 72%) as a white solid.

후처리

  1. washwashed each with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (eluted with 10-50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-eca5028d79de4ffe8c2cacdac2edd003
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455658B2

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