3-Aminopyridine → 4-Methyl-n-(2,2,2-trifluoro-1-{[(3-pyridinylamino)carbothioyl]amino}ethyl)benzamide

HRID 479473Notes

Reaction equation

HRID 479473 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([NH:15][CH:16]([N:21]=[C:22]=[S:23])[C:17]([F:20])([F:19])[F:18])=[O:14])=[CH:11][CH:10]=1>C1C=CC=CC=1>[CH3:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:15][CH:16]([NH:21][C:22]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[S:23])[C:17]([F:20])([F:19])[F:18])=[O:14])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 121503244-methyl-N-(2,2,2-trifluoro-1-isothiocyanatoethyl)benzamide

Product 1

HCID 99072854-Methyl-n-(2,2,2-trifluoro-1-{[(3-pyridinylamino)carbothioyl]amino}ethyl)benzamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 3-aminopyridine (145 mg, 1.54 mmol) in benzene (8 mL) at ambient temperature was treated with a solution of Example 1C (500 mg, 1.54 mmol) in benzene (1.5 mL). The reaction mixture was stirred for 1.5 hours, then concentrated to a nominal volume. The white solids which precipitated from solution were collected by filtration and were washed with diethyl ether. Recrystallization from 25% ethyl acetate/hexanes provided the desired product as a white solid.

Workup

  1. concentrationconcentrated to a nominal volume
  2. customThe white solids which precipitated from solution
  3. filtrationwere collected by filtration
  4. washwere washed with diethyl ether
  5. customRecrystallization from 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6e80e82d492d4cf3961678cbba023c38
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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