Oxalyl chloride → HCID 131735778, compound

HRID 2202767Notes

Reaction equation

HRID 2202767 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:16]([C:17]([F:20])([F:19])[F:18])=[C:15]([C:21](O)=[O:22])[CH:14]=[N:13]2)[CH2:8][C@@H:7]1[CH3:24])=[O:5])[CH3:2].[CH2:25]([O:27][C:28]([C@@H:30]1[CH2:35][CH2:34][C@@H:33]([N:36]2[C:40]([C:41]([F:44])([F:43])[F:42])=[C:39]([C:45](O)=[O:46])[CH:38]=[N:37]2)[CH2:32][C@H:31]1[CH3:48])=[O:29])[CH3:26].C(Cl)(=O)C([Cl:52])=O>C(Cl)Cl.CN(C=O)C>[Cl:52][C:21]([C:15]1[CH:14]=[N:13][N:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C@@H:7]([CH3:24])[CH2:8]2)[C:16]=1[C:17]([F:20])([F:19])[F:18])=[O:22].[Cl:52][C:45]([C:39]1[CH:38]=[N:37][N:36]([C@@H:33]2[CH2:34][CH2:35][C@@H:30]([C:28]([O:27][CH2:25][CH3:26])=[O:29])[C@H:31]([CH3:48])[CH2:32]2)[C:40]=1[C:41]([F:44])([F:43])[F:42])=[O:46]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 131735772HCID 131735772, compound

Product 1

HCID 131735778HCID 131735778, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a slightly cloudy mixture of 1-((1R,3R,4R)-4-(ethoxycarbonyl)-3-methylcyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid compound with 1-((1S,3S,4S)-4-(ethoxycarbonyl)-3-methylcyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (1:1) (0.300 g, 0.431 mmol) in DCM (17.23 ml) was added oxalyl chloride (0.091 ml, 1.077 mmol) followed by DMF (1 drop) and the light-yellow slightly cloudy reaction mixture was stirred at room temperature. After 1.5 h, the mixture was concentrated in vacuo to give (1R,2R,4R)-ethyl 4-(4-(chlorocarbonyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)-2-methylcyclohexane carboxylate compound with (1S,2S,4S)-ethyl 4-(4-(chlorocarbonyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)-2-methylcyclohexane carboxylate (1:1) as light-yellow syrup.

Workup

  1. customthe light-yellow slightly cloudy reaction mixture
  2. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-01728efe94794fb198f502e9ce4aa1a7
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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