Dichloromethane → HCID 20729730, compound

HRID 352169Notes

Reaction equation

HRID 352169 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.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C:30]1[C:34]([C:35]([OH:37])=O)=[C:33]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[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][CH2:23][CH2:24][C@H:30]([NH:31][C:35]([C:34]3[C:30]([C:24]4[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:23]=4[Cl:22])=[N:31][O:32][C:33]=3[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:37])[CH2:34]2)=[O:2])[CH:41]=[CH:40][CH:39]=[CH:38][CH:33]=1

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22713788HCID 22713788, compound

Product 1

HCID 20729730HCID 20729730, compoundYield 69%

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-chloro-6-fluoro-phenyl)-5-hexyl-isoxazole-4-carboxylic acid (0.117 g, 0.36 mmol), and dichloromethane (1.5 mL) gave the title compound (0.112 g, 69%) after column chromatography (silica gel, acetone/dichloromethane gradient). Mass Spectrum (FIA) (m/z) 540.5 [M+1].

Workup

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

Sources & evidence

ORD record
ord-f49e47a8ff264f03a9f4c7fd35c23c0c
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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