Butyl chloroformate → HCID 10116525, compound

HRID 1644843Notes

Reaction equation

HRID 1644843 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[N:25]=[N:24][CH:23]=[N:22]3)=[CH:16][CH:15]=2)[CH:6]=1)[CH:2]([CH3:4])[CH3:3].N1(C2C=CC=CN=2)CCCC1.Cl[C:38]([O:40][CH2:41][CH2:42][CH2:43][CH3:44])=[O:39].C(C1SC(S(NC(C)(C)C)(=O)=O)=C(C2C=CC(CN3N=NC=N3)=CC=2)C=1)C(C)C>N1C=CC=CC=1>[CH2:41]([O:40][C:38]([NH:13][S:10]([C:8]1[S:9][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][C:7]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[N:25]=[N:24][CH:23]=[N:22]2)=[CH:16][CH:15]=1)(=[O:12])=[O:11])=[O:39])[CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 4

HCID 61140Butyl chloroformateHCID 110190202-(Pyrrolidin-1-yl)pyridineHCID 66775093HCID 66775093, compoundHCID 66775478HCID 66775478, compound

Product 1

HCID 10116525HCID 10116525, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The crude product from step (d) above was dissolved in pyridine (1 mL, dried over 4 Å molecular sieve). Pyrrolidinopyridine (14 mg, 0.0095 mmol) and butyl chloroformate (120 μL, 0.97 mmol) were added to the mixture, which was then stirred for 30 hours 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 (35:1) as eluent yielded the title compound (24.9 mg, 0.052 mmol) in 54% yield (from 5-iso-butyl-N-tert-butyl-3-(4-tetrazol-2-ylmethylphenyl)thiophene-2-sulfonamide).

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-ab48aa8eabee4e87a68f06e3f1162a8a
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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