Triphenylphosphine → 1-[3-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-prop-2-ynyl]-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1253771

Reaction equation

HRID 1253771 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11](=[O:29])[NH:12][C:13]1[C:14]([CH3:28])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][CH2:26]O)=[CH:20][CH:19]=1)[CH3:9].[F:30][C:31]([F:43])([F:42])[C:32]1[NH:36][N:35]=[CH:34][C:33]=1[C:37]([O:39][CH2:40][CH3:41])=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:40]([O:39][C:37]([C:33]1[CH:34]=[N:35][N:36]([CH2:26][C:25]#[C:24][C:21]2[CH:22]=[CH:23][C:18]([C:17]3[O:16][N:15]=[C:14]([CH3:28])[C:13]=3[NH:12][C:11]([O:10][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH3:9])=[O:29])=[CH:19][CH:20]=2)[C:32]=1[C:31]([F:30])([F:42])[F:43])=[O:38])[CH3:41]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 596095Ethyl 3-(Trifluoromethyl)pyrazole-4-carboxylateHCID 70878238HCID 70878238, compound

Product 1

HCID 685296471-[3-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-prop-2-ynyl]-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {5-[4-(3-hydroxy-prop-1-ynyl)-phenyl]-3-methyl-isoxazol-4-yl}-carbamic acid 1-(2-chloro-phenyl)-ethyl ester (0.200 g, 0.49 mmol), ethyl 5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (0.101 g, 0.49 mmol), and triphenylphosphine (0.127 g, 0.49 mmol) in THF (4 mL) was added diisopropyl azodicarboxylate (0.10 mL, 0.49 mmol), and the reaction was stirred at room temperature for 2 hours. The mixture was concentrated, and the residue was purified by preparative HPLC to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3f35ad9b07114f939008e9fd17412984
Source dataset
uspto-grants-2013_06
Patent number
US08455499B2

Linked notes

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