Triethylamine → HCID 25099660, compound

HRID 2381942Notes

Reaction equation

HRID 2381942 reaction equation
[NH2:1][N:2]1[CH2:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:5][NH:4][C:3]1=[O:15].[C:16]1([C:22]2[N:27]=[CH:26][C:25]([C:28](O)=[O:29])=[CH:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.CN(C)CCCN=C=NCC.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[F:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH2:7][N:2]([NH:1][C:28]([C:25]3[CH:24]=[N:23][C:22]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[N:27][CH:26]=3)=[O:29])[C:3](=[O:15])[NH:4][N:5]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 7473892-Phenylpyrimidine-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68553173HCID 68553173, compound

Product 1

HCID 25099660HCID 25099660, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of 4-amino-6-(4-fluoro-phenyl)-4,5-dihydro-2H-1,2,4-triazin-3-one (0.26 g, 1.23 mmol), 2-phenyl-pyrimidine-5-carboxylic acid (0.25 g, 1.23 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.37 g, 1.94 mmol) in DMF (12 mL) is added Et3N (0.2 mL, 1.435 mmol) under N2 and the reaction mixture is stirred at rt for 49 h. The mixture is diluted with EtOAc (120 mL), and washed successively with saturated aqueous NH4Cl (2×50 mL), water (2×50 mL), and saturated aqueous NaCl (50 mL). The organic phase is dried (MgSO4), filtered, and concentrated in vacuo. The residue is triturated with EtOH (30 mL) to afford 2-phenyl-pyrimidine-5-carboxylic acid [6-(4-fluoro-phenyl)-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl]-amide (0.12 g, 25%). MS: 391 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 11.25 (s, 1H), 10.58 (s, 1H), 9.31 (s, 2H), 8.47 (dd, J=7.7, 1.8 Hz, 2 H), 7.70-7.86 (m, 2 H), 7.49-7.67 (m, 3H), 7.18-7.34 (m, 2H), 4.77.

Workup

  1. washwashed successively with saturated aqueous NH4Cl (2×50 mL), water (2×50 mL), and saturated aqueous NaCl (50 mL)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is triturated with EtOH (30 mL)

Sources & evidence

ORD record
ord-b30acbf278a7476ca456b71984a48513
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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