Butyl chloroformate → N-butyloxycarbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-butylthiophene-2-sulfonamide

HRID 1993841Notes

Reaction equation

HRID 1993841 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:17]=[C:16]([CH2:18][CH2:19][CH2:20][CH3:21])[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][CH2:42][CH2:43][CH3:44])=[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][CH2:19][CH2:20][CH3:21])=[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])[CH2:42][CH2:43][CH3:44]

Participants

5

Reactant 3

HCID 61140Butyl chloroformateHCID 110190202-(Pyrrolidin-1-yl)pyridineHCID 667751023-(4-Imidazol-1-ylmethylphenyl)-5-butylthiophene-2-sulfonamide

Product 1

HCID 10140383N-butyloxycarbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-butylthiophene-2-sulfonamideYield 10%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(4-Imidazol-1-ylmethylphenyl)-5-butylthiophene-2-sulfonamide (232 mg, 0.62 mmol; see step (d) above) was dissolved in pyridine (3 mL, dried over 4 Å molecular sieves). Pyrrolidinopyridine (91.6 mg, 0.618 mmol) and butyl chloroformate (785.7 μL, 0.618 mmol) were added to the mixture. The mixture was stirred overnight under a N2 atmosphere at room temperature. Evaporation and co-evaporation with acetonitrile to remove the solvents, followed by purification by column chromatography using 10% MeOH in chloroform as eluent, gave the title compound (29 mg, 0.061 mmol) in 10% yield.

Workup

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

Sources & evidence

ORD record
ord-a879d77acd53488a93e46624d48c1130
Source dataset
uspto-grants-2010_01
Patent number
US07652054B2

Reaction notes

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