Dichloromethane → n-{(1s,3r)-3-[(Phenylcarbonylamino)methyl]cyclohexyl}[3-(2,4-difluorophenyl)-5-methylisoxazol-4-yl]carboxamide

HRID 352168Notes

Reaction equation

HRID 352168 reaction equation
[C:1](O)([C:3](F)(F)F)=[O:2].ClCCl.CCN=C=N[CH2:16][CH2:17][CH2:18][N:19](C)C.[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[C:30]1[C:34]([C:35]([OH:37])=O)=[C:33]([CH3:38])[O:32][N:31]=1>CN(C1C=CN=CC=1)C.CC(C)=O.ClCCl>[C:3]1([C:1]([NH:19][CH2:18][C@@H:17]2[CH2:16][CH2:33][CH2:34][C@H:30]([NH:31][C:35]([C:34]3[C:30]([C:24]4[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=4[F:22])=[N:31][O:32][C:33]=3[CH3:38])=[O:37])[CH2:24]2)=[O:2])[CH:23]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22713986HCID 22713986, compound

Product 1

HCID 20729729n-{(1s,3r)-3-[(Phenylcarbonylamino)methyl]cyclohexyl}[3-(2,4-difluorophenyl)-5-methylisoxazol-4-yl]carboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

In a fashion similar to that described for preparation 108, a compound from preparation 105 (0.1 g, 0.3 mmol), TFA (2 mL), dichloromethane (1.5 mL), EDCI (0.086 g, 0.45 mmol), DMAP (0.007 g, 0.06 mmol), 3-(2,4-difluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid (0.086 g, 0.36 mmol), and dichloromethane (1.5 mL) gave the title compound (0.123 g, 90%) after column chromatography (silica gel, acetone/dichloromethane gradient). Mass Spectrum (FIA) (m/z) 454.2 [M+1].

Workup

  1. customIn a fashion similar to that described for preparation 108

Sources & evidence

ORD record
ord-233d926a1704468f98d672d892164937
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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