Butyl chloroformate → HCID 11994289, compound

HRID 1644838Notes

Reaction equation

HRID 1644838 reaction equation
N1(C2C=CC=CN=2)CCCC1.Cl[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14].[N:20]1([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[C:36]([CH2:38][CH:39]([CH3:41])[CH3:40])[CH:35]=[CH:34][C:33]=3[S:42]([NH:45]C(C)(C)C)(=[O:44])=[O:43])=[CH:28][CH:27]=2)[CH:24]=[CH:23][N:22]=[CH:21]1>N1C=CC=CC=1>[CH2:16]([O:15][C:13]([NH:45][S:42]([C:33]1[CH:34]=[CH:35][C:36]([CH2:38][CH:39]([CH3:41])[CH3:40])=[CH:37][C:32]=1[C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[CH:27][CH:28]=1)(=[O:43])=[O:44])=[O:14])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 61140Butyl chloroformateHCID 110190202-(Pyrrolidin-1-yl)pyridineHCID 11994152HCID 11994152, compound

Product 1

HCID 11994289HCID 11994289, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The crude product from step (d) above was dissolved in pyridine (2 mL, dried over 4 Å molecular sieve). Pyrrolidinopyridine (36 mg, 0.024 mmol) and butyl chloroformate (276 μL, 2.23 mmol) were added to the mixture, which was then stirred for 30 h under N2 (g) at room temperature. The solvent was removed in vacuo and then co-evaporated with acetonitrile. Purification using column chromatography with CHCl3:MeOH (10:1) as eluent yielded the title compound (66.7 mg, 0.142 mmol) in 68% yield (from 2-(4-imidazol-1-ylmethylphenyl)-4-iso-butyl-N-tert-butylbenzene-sulfonamide).

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-0d6a125cfb4244cf9d71b3025596f431
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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