Butyl chloroformate → HCID 10184083, compound

HRID 1993858Notes

Reaction equation

HRID 1993858 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][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]=[N:4][CH:3]=[N:2]1.Cl[C:27]([O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:28]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C.C(OCC)(=O)C>[CH2:30]([O:29][C:27]([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]=[N:4][CH:3]=[N:2]2)=[CH:8][CH:9]=1)(=[O:23])=[O:24])=[O:28])[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 2

HCID 61140Butyl chloroformateHCID 66775157HCID 66775157, compound

Product 1

HCID 10184083HCID 10184083, compoundYield 9.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

59 mg (0.16 mmol) of the crude 3-(4-[1,2,4]triazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide from step (c) above was mixed with butyl chloroformate (31 μL, 0.24 mmol) and 4-dimethylaminopyridine (2 mg, 16 μmol) in 5 mL of triethylamine at 0° C. The reaction mixture was stirred overnight and then diluted with ethyl acetate, washed with water and dried over K2CO3. The reaction mixture was then separated on a silica column (dichloromethane+15% methanol), circular chromatography (dichloromethane+10-15% methanol and preparative LC-MS to yield 7.0 mg of the title compound (9% isolated yield).

Workup

  1. washwashed with water
  2. dry with materialdried over K2CO3
  3. customThe reaction mixture was then separated on a silica column (dichloromethane+15% methanol), circular chromatography (dichloromethane+10-15% methanol and preparative LC-MS

Sources & evidence

ORD record
ord-d3e3e7a879844d1eb71a5ab14dfaaa71
Source dataset
uspto-grants-2010_01
Patent number
US07652054B2

Reaction notes

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