Triethylamine → HCID 42633472, 화합물

HRID 1009042노트

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HRID 1009042 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([S:7](=[O:10])(=[O:9])[NH2:8])[S:4][C:3]=1[CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15].Cl[C:18](OC1C=CC=CC=1)=[O:19].C(N(CC)CC)C.[Br:34][C:35]1[S:39][C:38]([NH2:40])=[N:37][C:36]=1[CH3:41]>C(#N)C>[C:14]([O:13][CH2:12][CH2:11][C:3]1[S:4][C:5]([S:7]([NH:8][C:18](=[O:19])[NH:40][C:38]2[S:39][C:35]([Br:34])=[C:36]([CH3:41])[N:37]=2)(=[O:10])=[O:9])=[CH:6][C:2]=1[CH3:1])(=[O:16])[CH3:15]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 129543735-Bromo-4-methyl-1,3-thiazol-2-amineHCID 67273589HCID 67273589, 화합물

생성물 1

HCID 42633472HCID 42633472, 화합물수율 50.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

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온도
60 °C

실험 절차

Acetic acid 2-(3-methyl-5-sulfamoyl-thiophen-2-yl)-ethyl ester (0.120 g, 0.456 mmol) was dissolved in 4.5 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.057 g, 1.00 eq.) and triethylamine (0.159 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1 h. 5-Bromo-4-methyl-thiazol-2-ylamine (0.088 g, 1.00 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, ethyl acetate/5% MeOH), followed by crystallization from ethyl acetate/heptane, yielded finally 0.089 g of the title compound as light brown solid.

후처리

  1. additionwas then added
  2. temperatureCooling
  3. additionpouring
  4. extractionice/NH4Cl, twofold extraction with ethyl acetate
  5. washwashing with brine
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  7. customfollowed by crystallization from ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-8f8c23eb95994c4d97d81d5ba567246f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973051B2

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