Triethylamine → 2-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-benzoic acid formyl hydrazide

HRID 927007Notes

Reaction equation

HRID 927007 reaction equation
[C:1]([C:4]1[CH:5]([C:23]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][C:24]=2[C:25]([OH:27])=O)[N:6]([CH3:22])[C:7](=[O:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2].C(N(CC)CC)C.F[B-](F)(F)F.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.[CH:63]([NH:65][NH2:66])=[O:64]>CN(C)C=O>[CH:63]([N:65]([C:25](=[O:27])[C:24]1[CH:28]=[C:29]([C:32]#[N:33])[CH:30]=[CH:31][C:23]=1[CH:5]1[C:4]([C:1](=[O:3])[CH3:2])=[C:9]([CH3:10])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)[C:7](=[O:21])[N:6]1[CH3:22])[NH2:66])=[O:64]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12229Hydrazinecarboxaldehyde2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118691679US9290457, Intermediate 62×

Product 1

HCID 1186916972-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-benzoic acid formyl hydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-benzoic acid (intermediate 6) (75.0 mg, 0.16 mmol)) and triethylamine (57.1 μL, 0.41 mmol) are suspended in N,N-dimethylformamide (2 mL), stirred for 5 min and N,N,N′,N′-tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (63.2 mg, 0.20 mmol) is added. The mixture is stirred for 10 min and formic acid hydrazide (10.8 mg, 0.18 mmol) is added. The mixture is stirred overnight at room temperature. Another equivalent of formic acid hydrazide is added to bring the reaction to completion. The crude product is purified by reversed phase HPLC. Yield 30 mg; ESI mass spectrum [M+H]+=500; Retention time HPLC: 0.94 min (HPLC method Z018_S04).

Workup

  1. stirringThe mixture is stirred for 10 min
  2. stirringThe mixture is stirred overnight at room temperature
  3. customthe reaction to completion
  4. customThe crude product is purified by reversed phase HPLC
  5. custom0.94 min (HPLC method Z018_S04)

Sources & evidence

ORD record
ord-1d77e122caaa47c79980859f033ce0ce
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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