Hydrochloric Acid → HCID 135928045, compound

HRID 1020199Notes

Reaction equation

HRID 1020199 reaction equation
[OH:1][NH:2][C:3]([C:5]1[S:6][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:8][CH:9]=1)=[NH:4].[C:32]1([O:38]C(Cl)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.Cl>ClCCl.C(#N)C.C(N(CC)CC)C>[F:29][C:28]([F:31])([F:30])[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[S:6][C:5]([C:3]4[NH:4][C:32](=[O:38])[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178513363HCID 178513363, compound

Product 1

HCID 135928045HCID 135928045, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

152 mg crude N-Hydroxy-5-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-thiophene-2-carboxamidine were dissolved in 10 ml dichloromethane. 1.0 ml triethylamine and 43 ml phenylchloroformate were added at 0° C. and the mixture stirred at 0° C. for thirty minutes. The mixture was diluted by the addition of 10 ml acetonitrile and 97 μl 1,8-diazabicyclo[5.4.0]undec-7-ene were added. The mixture was stirred at 0° C. for 15 minutes. Then the mixture was poured on 100 ml 1M HCl and extracted five times with portions of 50 ml dichloromethane. The combined organic extracts were washed with 100 ml saturated NaHCO3 solution. The organic layer was then dried over MgSO4. The solvent was removed in vacuo. The resulting crude material was purified by chromatography on silica gel to obtain 125 mg 3-{5-[5-(4-Trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-thiophen-2-yl}-4H-[1,2,4]oxadiazol-5-one. C21H14F3N3O4S2 (493.49), MS (ESI−): 492.2 (M−H+).

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at 0° C. for 15 minutes
  3. extractionextracted five times with portions of 50 ml dichloromethane
  4. washThe combined organic extracts were washed with 100 ml saturated NaHCO3 solution
  5. dry with materialThe organic layer was then dried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customThe resulting crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6bd4982e13254240aa8dd59732a79aa0
Source dataset
uspto-grants-2014_05
Patent number
US08716317B2

Reaction notes

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