Pyridine → HCID 135928017, compound

HRID 2192284Notes

Reaction equation

HRID 2192284 reaction equation
[OH:1][NH:2][C:3](=[NH:32])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=4)=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.N1C=CC=CC=1.[C:39]1([O:45]C(Cl)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>ClCCl.C(#N)C>[F:29][C:28]([F:31])([F:30])[C:25]1[N:24]=[CH:23][C:22]([C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[N:13]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]4[NH:32][C:39](=[O:45])[O:1][N:2]=4)=[CH:9][CH:8]=2)(=[O:11])=[O:12])[CH2:14][CH2:15]3)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178513364HCID 178513364, compound

Product 1

HCID 135928017HCID 135928017, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

550 mg crude N-Hydroxy-4-[5-(6-trifluoromethyl-pyridin-3-yl)-2,3-dihydro-indole-1-sulfonyl]-benzamidine were dissolved in 20 ml dichloromethane. 0.17 ml pyridine and 0.18 ml phenylchloroformate were added and the mixture stirred at room temperature for ten minutes. The mixture was diluted by the addition of 20 ml acetonitrile and 0.89 ml 1,8-diazabicyclo[5.4.0]undec-7-ene were added. The mixture was stirred at room temperature for 15 minutes. The mixture was evaporated in vacuo and the resulting crude material was purified by reversed phase HPLC to obtain 175 mg 3-{4-[5-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-indole-1-sulfonyl]-phenyl}-4H-[1,2,4]oxadiazol-5-one.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at room temperature for 15 minutes
  3. customThe mixture was evaporated in vacuo
  4. customthe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-b09153b9d98a492c937fc8aab3bea398
Source dataset
uspto-grants-2012_12
Patent number
US08329725B2

Reaction notes

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