Triethylamine → US9290457, Example 1.5

HRID 927008Notes

Reaction equation

HRID 927008 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.[N:48]1(OC(N(C)C)=[N+](C)C)[C:52]2N=CC=[CH:56][C:51]=2N=N1>CN(C)C=O>[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]([NH:48][CH2:52][C:51]#[CH:56])=[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:18])([F:19])[F:20])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×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 118691671US9290457, Example 1.5

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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) (70 mg, 0.15 mmol) and triethylamine (35 μL, 0.25 mmol) are suspended in N,N-dimethylformamide (1.5 mL) and the mixture is shaken for 5 min. A solution of O-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (61.1 mg, 0.16 mmol) in N,N-dimethylformamide (0.5 mL) and triethylamine (35 μL, 0.25 mmol) is added and the reaction mixture is shaken for 1.5 h at room temperature. The product is purified by reversed phase HPLC. Yield 48 mg; ESI mass spectrum [M+H]+=495; Retention time HPLC: 0.99 min (HPLC method Z011_S03).

Workup

  1. stirringthe reaction mixture is shaken for 1.5 h at room temperature
  2. customThe product is purified by reversed phase HPLC
  3. custom0.99 min (HPLC method Z011_S03)

Sources & evidence

ORD record
ord-bddc3044ca164e34862b0b0800fe13ee
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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