3-(Trifluoromethyl)benzoic acid → HCID 67329761, compound

HRID 2092588Notes

Reaction equation

HRID 2092588 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([N:8]2[CH2:24][CH2:23][C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:18]=[N:19][CH:20]=[N:21][CH:22]=4)[N:14]=[CH:15][C:10]=3[CH2:9]2)[CH:7]=1.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](O)=[O:32].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH3:25][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][CH:36]=[C:28]([C:27]([F:26])([F:37])[F:38])[CH:29]=2)=[CH:7][C:6]=1[N:8]1[CH2:24][CH2:23][C:11]2[N:12]=[C:13]([NH:16][C:17]3[CH:18]=[N:19][CH:20]=[N:21][CH:22]=3)[N:14]=[CH:15][C:10]=2[CH2:9]1

Participants

7

Reactant 4

HCID 99633-(Trifluoromethyl)benzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67329993HCID 67329993, compound

Product 1

HCID 67329761HCID 67329761, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [6-(5-Amino-2-methyl-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-pyrimidin-5-yl-amine (50.0 mg, 0.15 mmol), 3-Trifluoromethylbenzoic acid (28.5 mg, 0.15 mmol), and DIPEA (78 μl, 0.45 mmol) in DMF was added HATU (59 mg, 0.15 mmol), and the reaction mixture was stirred for 3 hour at room temperature. The reaction mixture is diluted with ethyl acetate and washed with 5% aqueous sodium bisulphate solution, saturated aqueous sodium bicarbonate solution and brine. The organic layer is dried over sodium sulphate and concentrated under reduced pressure. The crude product obtained was purified by column chromatography (SiO2, 2-10% methanol in chloroform) to give 49.75 mg (65.6%) of N-{4-Methyl-3-[2-(pyrimidin-5-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-phenyl}-3-trifluoromethyl benzamide [17] as a pale yellow solid.

Workup

  1. washwashed with 5% aqueous sodium bisulphate solution, saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialThe organic layer is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product obtained
  5. customwas purified by column chromatography (SiO2, 2-10% methanol in chloroform)

Sources & evidence

ORD record
ord-f5771e63a2d44a4489933245f304224a
Source dataset
uspto-grants-2013_05
Patent number
US08440679B2

Reaction notes

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