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 acetyl hydrazide

HRID 927009Notes

Reaction equation

HRID 927009 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](O)=[O:26])[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[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:65]([NH:68][NH2:69])(=[O:67])[CH3:66]>CN(C)C=O>[C:65]([N:68]([C:25](=[O:26])[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])[NH2:69])(=[O:67])[CH3:66]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14039Acetohydrazide2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118691679US9290457, Intermediate 62×

Product 1

HCID 1186916732-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-benzoic acid acetyl 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-m 4-yl]-5-cyano-benzoic acid (intermediate 6) (47.0 mg, 0.10 mmol)) and triethylamine (35.8 μL, 0.26 mmol) are suspended in N,N-dimethylformamide (2 mL), stirred for 5 min and O-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (41.0 mg, 0.11 mmol) is added. The mixture is stirred for 10 min and acetic acid hydrazide (12.2 mg, 0.16 mmol) is added. The mixture is stirred overnight at room temperature. Another equivalent of acetic acid hydrazide is added to bring the reaction to completion. The crude product is purified by reversed phase HPLC. Yield 15 mg; ESI mass spectrum [M+H]+=514; Retention time HPLC: 0.95 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. custom0.95 min (HPLC method Z018_S04)

Sources & evidence

ORD record
ord-72bde5df71314c47819986c808842088
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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