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Isobutyl chloroformate → N-iso-Butyloxycarbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide

HRID 1993834
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HRID 1993834 반응식
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:17]=[C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[S:15][C:14]=3[S:22]([NH2:25])(=[O:24])=[O:23])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.N1(C2C=CC=CN=2)CCCC1.Cl[C:38]([O:40][CH2:41][CH:42]([CH3:44])[CH3:43])=[O:39]>N1C=CC=CC=1>[CH2:41]([O:40][C:38]([NH:25][S:22]([C:14]1[S:15][C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:17][C:13]=1[C:10]1[CH:11]=[CH:12][C:7]([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:8][CH:9]=1)(=[O:24])=[O:23])=[O:39])[CH:42]([CH3:44])[CH3:43]
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참가 물질

5

반응물 3

HCID 62365Isobutyl chloroformateHCID 110190202-(Pyrrolidin-1-yl)pyridineHCID 113947443(4-Imidazol-1-ylmethylphenyl)5-iso-butylthiophene-2 sulfonamide

생성물 1

HCID 10116410N-iso-Butyloxycarbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide수율 71.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
50 °C

실험 절차

30 mg of crude 3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide (see Example 1(f) above) was dissolved in pyridine (1 mL, dried over 4 Å molecular sieve) and cooled on ice. Pyrrolidinopyridine (11.8 mg, 0.080 mmol) and iso-butyl chloroformate (103.6 μL, 0.80 mmol) were then added to the mixture. The mixture was stirred overnight under a N2 atmosphere at 50° C. Evaporation and co-evaporation with acetonitrile to remove the solvents, followed by purification by column chromatography using 10% MeOH in CHCl3 as eluent gave the title compound (27 mg, 0.057 mmol) in 71% yield.

후처리

  1. temperaturecooled on ice
  2. customEvaporation and co-evaporation with acetonitrile
  3. customto remove the solvents
  4. customfollowed by purification by column chromatography

출처 및 근거

ORD 기록
ord-ebca3ddfa41347e387bf1ded7a518655
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07652054B2

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