Acetic Acid → HCID 178461007, compound

HRID 1486589Notes

Reaction equation

HRID 1486589 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:13]=[C:12]([NH2:14])[NH:11][N:10]=2)[CH:5]=[C:4]([C:15]([F:18])([F:17])[F:16])[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])=[CH:21][CH:20]=1.[CH:31]([C:33]1[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:35][CH:34]=1)=O.C(O)(=O)C.Cl>CO>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:13]=[C:12]([NH:14][CH2:31][C:33]3[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])=[CH:35][CH:34]=3)[NH:11][N:10]=2)[CH:5]=[C:4]([C:15]([F:18])([F:16])[F:17])[C:3]=1[C:19]1[CH:20]=[CH:21][C:22]([S:25]([CH:28]([CH3:30])[CH3:29])(=[O:26])=[O:27])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 2751588Tert-butyl 4-formylbenzoateHCID 90391302HCID 90391302, compound

Product 1

HCID 178461007HCID 178461007, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N3-(2-chloro-4′-(isopropylsulfonyl)-6-(trifluoromethyl)biphenyl-4-yl)-1H-1,2,4-triazole-3,5-diamine (135 mg, 294 μmol) in MeOH (3.5 ml) was added tert-butyl 4-formylbenzoate (85 mg, 412 μmol) followed by acetic acid (52.4 mg, 50 μl, 873 μmol). The reaction was stirred at room temperature for 15 minutes, 2-picoline borane complex (42.4 mg, 396 μmol) was added and the stirring was continued for 3 days. The reaction mixture was poured into 0.1N HCl solution (20 ml) and the resulting suspension was filtered to collect the solid. The crude material was purified by flash chromatography (silica gel, 24 g, 3% to 5% MeOH in DCM) to afford a white solid as desired product (94 mg, 49% yield). MS +m/z: 650 (M+H)+

Workup

  1. addition2-picoline borane complex (42.4 mg, 396 μmol) was added
  2. waitthe stirring was continued for 3 days
  3. filtrationthe resulting suspension was filtered
  4. customto collect the solid
  5. customThe crude material was purified by flash chromatography (silica gel, 24 g, 3% to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-30f1e78c72894bf69793cffdcad818a4
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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