Acetic Acid → HCID 178450685, compound

HRID 1486587Notes

Reaction equation

HRID 1486587 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:15]=[C:14]([Cl:16])[C:11]([C:12]#[N:13])=[C:10]([Cl:17])[CH:9]=2)[N:3]=1.[CH:18]([C:20]1[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][CH:21]=1)=O.C(O)(=O)C.Cl>CO>[Cl:16][C:14]1[CH:15]=[C:8]([NH:7][C:4]2[N:3]=[C:2]([NH:1][CH2:18][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[CH:22][CH:21]=3)[NH:6][N:5]=2)[CH:9]=[C:10]([Cl:17])[C:11]=1[C:12]#[N:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 2751588Tert-butyl 4-formylbenzoateHCID 727067564-(5-amino-1H-1,2,4-triazol-3-ylamino)-2,6-dichlorobenzonitrile

Product 1

HCID 178450685HCID 178450685, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-benzonitrile (60 mg, 223 μmol) in MeOH (3.5 ml) was added tert-butyl 4-formylbenzoate (55.2 mg, 268 μmol) followed by acetic acid (21.0 mg, 20 μl, 349 μmol). The reaction was stirred at room temperature for 15 minutes, 2-picoline borane complex (32.2 mg, 349 μmol) was added and the stirring was continued for 4 days. The reaction mixture was poured into 0.1N HCl solution (20 ml) and let stand. The resulting suspension was filtered to collect the solid. Purification by super fluid chromatography and trituration from acetonitrile afforded a white solid as desired product (54.5 mg, 53% yield). MS +m/z: 459 (M+H)+

Workup

  1. addition2-picoline borane complex (32.2 mg, 349 μmol) was added
  2. waitthe stirring was continued for 4 days
  3. filtrationThe resulting suspension was filtered
  4. customto collect the solid
  5. customPurification by super fluid chromatography and trituration from acetonitrile

Sources & evidence

ORD record
ord-6f4e9985294443d3b01cef9b016a78cc
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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