Butyl chloroformate → HCID 11994289, compound

HRID 1993846Notes

Reaction equation

HRID 1993846 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH:16]=[CH:15][C:14]=3[S:23]([NH2:26])(=[O:25])=[O:24])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.N1(C2C=CC=CN=2)CCCC1.Cl[C:39]([O:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:40].N1(CC2C=CC(C3C=C(CC(C)C)C=CC=3S(NC(C)(C)C)(=O)=O)=CC=2)C=CN=C1>N1C=CC=CC=1>[CH2:42]([O:41][C:39]([NH:26][S:23]([C:14]1[CH:15]=[CH:16][C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:18][C:13]=1[C:10]1[CH:9]=[CH:8][C:7]([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:12][CH:11]=1)(=[O:24])=[O:25])=[O:40])[CH2:43][CH2:44][CH3:45]

Participants

6

Reactant 4

HCID 61140Butyl chloroformateHCID 110190202-(Pyrrolidin-1-yl)pyridineHCID 11994152HCID 11994152, compoundHCID 68677900HCID 68677900, 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-6d361bd142ee461e82f1ee6c3872c259
Source dataset
uspto-grants-2010_01
Patent number
US07652054B2

Reaction notes

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