Butyl chloroformate → HCID 10116525, compound

HRID 1993851Notes

Reaction equation

HRID 1993851 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-c0b0404af3514f2ea30d5007b4a1de89
Source dataset
uspto-grants-2010_01
Patent number
US07652054B2

Reaction notes

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