Diisopropylethylamine → Ethyl 5-[({[3-(6-fluoro-quinolin-2-yl)-3-azabicyclo[3.1.0]hex-6-yl]carbamoyl}oxy)-methyl]isoxazole-3-carboxylate

HRID 538398Notes

Reaction equation

HRID 538398 reaction equation
[CH:1]12[CH:6]([NH:7][C:8]([O:10][CH2:11][C:12]3[O:16][N:15]=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=3)=[O:9])[CH:5]1[CH2:4][NH:3][CH2:2]2.C(N(CC)C(C)C)(C)C.Cl[C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([F:42])[CH:38]=2)[N:33]=1>FC(F)(F)C([O-])=O>[F:42][C:37]1[CH:38]=[C:39]2[C:34](=[CH:35][CH:36]=1)[N:33]=[C:32]([N:3]1[CH2:4][CH:5]3[CH:1]([CH:6]3[NH:7][C:8]([O:10][CH2:11][C:12]3[O:16][N:15]=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=3)=[O:9])[CH2:2]1)[CH:41]=[CH:40]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 150594332-Chloro-6-fluoroquinolineHCID 67606011HCID 67606011, compound

Product 1

HCID 67607896Ethyl 5-[({[3-(6-fluoro-quinolin-2-yl)-3-azabicyclo[3.1.0]hex-6-yl]carbamoyl}oxy)-methyl]isoxazole-3-carboxylateYield 36.5%

Reagents, catalysts & solvents 1

HCID 84468TrifluoroacetateSolvent

Procedure

Starting from 1.55 g (3.79 mmol) of ethyl 5-{[(3-azabicyclo[3.1.0]hex-6-ylcarbamoyl)oxy]methyl}isoxazole-3-carboxylate in trifluoroacetate form, 1.98 ml (11.37 mmol) of N,N-diisopropylethylamine, and 0.68 g (3.79 mmol) of 2-chloro-6-fluoro-quinoline, and eluting with a 99/1 to 98/2 mixture of dichloromethane and methanol, 0.61 g (36%) of product is obtained in the form of an orange oil.

Workup

  1. washeluting with a 99/1 to 98/2 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-5f232473248745e89c9189f1f932d7f6
Source dataset
uspto-grants-2014_10
Patent number
US08865738B2

Reaction notes

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