Pyridine → HCID 135924144, compound

HRID 1921239Notes

Reaction equation

HRID 1921239 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:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=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:30][C:28]([F:31])([F:29])[C:25]1[CH:26]=[CH:27][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:23][CH:24]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178513362HCID 178513362, compound

Product 1

HCID 135924144HCID 135924144, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

550 mg N-hydroxy-4-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-benzamidine were dissolved in 10 ml dichloromethane. 0.17 ml pyridine and 0018 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 330 mg 3-{4-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-phenyl}-4H-[1,2,4]oxadiazol-5-one as an amorphous lyophilisate.

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-e4e6e4d1c7454c678ce1a96d1cbfe34a
Source dataset
uspto-grants-2012_05
Patent number
US08173674B2

Reaction notes

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