Diisopropylethylamine → Ethyl 5-[2-(6-Fluoroquinolin-2-yl)-2-azaspiro[3.3]hept-6-ylcarbamoyloxymethyl]isoxazole-3-carboxylate

HRID 336546Notes

Reaction equation

HRID 336546 reaction equation
FC(F)(F)C(O)=O.[CH2:8]1[C:11]2([CH2:14][CH:13]([NH:15][C:16]([O:18][CH2:19][C:20]3[O:24][N:23]=[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:21]=3)=[O:17])[CH2:12]2)[CH2:10][NH:9]1.Cl[C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36]([F:41])[CH:37]=2)[N:32]=1.C(N(CC)C(C)C)(C)C>ClCCl.CO>[F:41][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][CH:35]=1)[N:32]=[C:31]([N:9]1[CH2:10][C:11]3([CH2:12][CH:13]([NH:15][C:16]([O:18][CH2:19][C:20]4[O:24][N:23]=[C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:21]=4)=[O:17])[CH2:14]3)[CH2:8]1)[CH:40]=[CH:39]2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 150594332-Chloro-6-fluoroquinolineHCID 68000734Ethyl 5-(2-azaspiro[3.3]hept-6-ylcarbamoyloxymethyl)isoxazole-3-carboxylate trifluoroacetate

Product 1

HCID 68000144Ethyl 5-[2-(6-Fluoroquinolin-2-yl)-2-azaspiro[3.3]hept-6-ylcarbamoyloxymethyl]isoxazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The process is performed according to the procedure described in Example 2 (step 2.6.). Starting with 0.43 g (1.03 mmol) of ethyl 5-(2-azaspiro[3.3]hept-6-ylcarbamoyloxymethyl)isoxazole-3-carboxylate trifluoroacetate, obtained in step 11.8., 0.187 g (1.03 mmol) of 2-chloro-6-fluoroquinoline and 0.399 g (3.09 mmol) of N,N-diisopropylethylamine, and after chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol, 0.15 g of pure product in the form of a beige-coloured solid is thus obtained.

Workup

  1. customobtained in step 11.8
  2. customis thus obtained

Sources & evidence

ORD record
ord-3bcf12f5201843a29d4239b248f9fbcc
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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