Triethylamine → 2-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-cyano-6-methyl-phenyl]-amide

HRID 1819274Notes

Reaction equation

HRID 1819274 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:14][C:15](=[O:26])[C:16]4[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[C:19]([CH3:25])[C:17]=4[N:18]=3)=[CH:11][C:10]([C:27]([F:30])([F:29])[F:28])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[C:32]1([NH2:38])([CH:35]2[CH2:37][CH2:36]2)[CH2:34][CH2:33]1.C(N(CC)CC)C>O1CCCC1>[C:32]1([NH:38][C:15]([C:16]2[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[C:19]([CH3:25])[C:17]=2[NH:18][C:13]([C:12]2[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=[C:10]([C:27]([F:30])([F:29])[F:28])[CH:11]=2)=[O:14])=[O:26])([CH:35]2[CH2:37][CH2:36]2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53433499(1,1'-Bi(cyclopropan))-1-amine hydrochlorideHCID 668578402-[1-(3-Chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4-oxo-4H-3,1-benzoxazine-6-carbonitrile

Product 1

HCID 709604762-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-cyano-6-methyl-phenyl]-amideYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-8-methyl-4-oxo-4H-benzo[d][1,3]oxazine-6-carbonitrile (1.2 g, 2,8 mmol) (prepared according to WO 04/067528) in tetrahydrofuran (40 ml), is added bicyclopropyl-1-ylamine hydrochloride (0.6 g, 4.2 mmol) and 1.2 ml (8.4 mmol) triethylamine, and the solution is heated at a temperature of 60° C. for 8 h. The solution is cooled down to ambient temperature and the solvent is evaporated. Then the mixture is triturated in 100 ml water and the crystals are washed with water and ether to afford 0.85 g of the title compound. The mother liquor is evaporated and a second crop of crystals is obtained by crystallisation in diisopropylether to afford 0.46 g of the title compound (F: 270-272° C.).

Workup

  1. temperatureThe solution is cooled down to ambient temperature
  2. customthe solvent is evaporated
  3. customThen the mixture is triturated in 100 ml water
  4. washthe crystals are washed with water and ether

Sources & evidence

ORD record
ord-bbdcfb4591d64749a62b93ac17e11ff3
Source dataset
uspto-grants-2009_10
Patent number
US07601743B2

Reaction notes

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