Pyridine → HCID 178513700, compound

HRID 1049873Notes

Reaction equation

HRID 1049873 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6](Cl)=[O:7])=[N:2]1.[NH2:9][C:10]1[S:11][CH:12]=[CH:13][C:14]=1[C:15]([NH2:17])=[O:16].N1C=CC=CC=1>CC#N.CN(C1C=CN=CC=1)C>[C:15]([C:14]1[CH:13]=[CH:12][S:11][C:10]=1[NH:9][C:6]([C:3]1[CH:4]=[CH:5][NH:1][N:2]=1)=[O:7])(=[O:16])[NH2:17]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6994952-Aminothiophene-3-carboxamideHCID 178521118HCID 178521118, compound

Product 1

HCID 178513700HCID 178513700, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 1H-Pyrazole-3-carbonyl chloride (5 mmol) in MeCN (5 mL) is added drop wise to a solution of 2-amino-thiophene-3-carboxylic acid amide (570 mg, 4 mmol), pyridine (0.5 mL, 6 mmol) and DMAP (25 mg, 0.20 mmol) in MeCN (5 mL). The resulting solution is than stirred at 60° C. over 2 days. Next, the mixture is quenched with aqueous NaHCO3. Evaporation of the MeCN gives a suspension that is filtered, the cake is dried, and used as such.

Workup

  1. customNext, the mixture is quenched with aqueous NaHCO3
  2. customEvaporation of the MeCN
  3. customgives a suspension that
  4. filtrationis filtered
  5. customthe cake is dried

Sources & evidence

ORD record
ord-0b6db1ff1f5a4412bf11f71ee0815bdd
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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