Acetic Acid → HCID 178527355, compound

HRID 1486580Notes

Reaction equation

HRID 1486580 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[N:16]1([S:21]([C:24]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]1.C(O)(=O)C.Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:28][C:27]3[CH:30]=[CH:31][C:24]([S:21]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)(=[O:23])=[O:22])=[CH:25][CH:26]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 585641144-(Pyrrolidine-1-sulfonyl)benzaldehydeHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazole

Product 1

HCID 178527355HCID 178527355, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (100 mg, 410 μmol) in MeOH (3.5 ml) was added 4-(pyrrolidin-1-ylsulfonyl)benzaldehyde (118 mg, 492 μmol) followed by acetic acid (36.7 mg, 35 μl, 611 μmol). The reaction was stirred at room temperature for 15 minutes, 2-picoline borane complex (65.7 mg, 615 μmol) was added and the stirring was continued for 6 days. The reaction mixture was poured into 0.1N HCl solution (25 ml) to give a suspension, which was filtered to give a white solid as desired product (151 mg, 79% yield). MS +m/z: 467 (M+H)+

Workup

  1. addition2-picoline borane complex (65.7 mg, 615 μmol) was added
  2. waitthe stirring was continued for 6 days
  3. customto give a suspension, which
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-002cf52617194f6684080ba9e83afde4
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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