Dichloromethane → HCID 57595458, compound

HRID 1785942Notes

Reaction equation

HRID 1785942 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5](C(Cl)=O)=[CH:4][CH:3]=1.[F:11][C:12]([F:28])([F:27])[C:13]1[CH:17]=[CH:16][N:15]([C:18]2[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=2)[N:14]=1.F[C:30](F)(F)[C:31]1[CH:35]=[CH:34][N:33]([C:36]2[CH:44]=[CH:43][C:39](C(O)=O)=[CH:38][CH:37]=2)[N:32]=1.[C:47](Cl)(=O)[C:48](Cl)=[O:49].C(Cl)[Cl:54]>CN(C=O)C>[Cl:54][C:39]1[CH:38]=[CH:37][C:36]([N:33]([C@H:34]2[C:3]3[C:2](=[CH:10][CH:9]=[CH:5][CH:4]=3)[N:32]([C:22](=[O:23])[C:21]3[CH:25]=[CH:26][C:18]([N:15]4[CH:16]=[CH:17][C:13]([C:12]([F:28])([F:27])[F:11])=[N:14]4)=[CH:19][CH:20]=3)[C@@H:31]([CH3:30])[CH2:35]2)[C:48](=[O:49])[CH3:47])=[CH:44][CH:43]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 678794-Fluorobenzoyl chlorideHCID 27806964-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoic acid2×HCID 27807004-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoyl chloride

Product 1

HCID 57595458HCID 57595458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1-{4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoyl}-1,2,3,4-tetrahydroquinolin-4-yl)acetamide was prepared following general procedure A, substituting 4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoyl chloride for 4-fluorobenzoyl chloride. (4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoyl chloride was prepared in one step from 4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoic acid. 4-[3-(Trifluoromethyl)-1H-pyrazol-1-yl]benzoic acid was treated with oxalyl chloride in DCM and catalytic DMF to afford 4-[3-(trifluoromothyl)-1H-pyrazol-1-yl]benzoyl chloride in decent yield). The rest of the procedures were followed as indicated in general procedure A to afford N-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1-{4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoyl}-1,2,3,4-tetrahydroquinolin-4-yl)acetamide.

Workup

  1. customN-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1-{4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoyl}-1,2,3,4-tetrahydroquinolin-4-yl)acetamide was prepared

Sources & evidence

ORD record
ord-516f5754b7e74eee9937bef93f434c35
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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