Methylamine → [3-(Methylcarbamoyl)isoxazol-5-yl]methyl [3-(6-fluoro-quinolin-2-yl)-3-azabicyclo[3.1.0]hex-6-yl]carbamate

HRID 538399Notes

Reaction equation

HRID 538399 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH:16]3[CH:14]([CH:15]3[NH:18][C:19]([O:21][CH2:22][C:23]3[O:27][N:26]=[C:25]([C:28](OCC)=[O:29])[CH:24]=3)=[O:20])[CH2:13]1)[CH:6]=[CH:5]2.[CH3:33][NH2:34]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH:16]3[CH:14]([CH:15]3[NH:18][C:19](=[O:20])[O:21][CH2:22][C:23]3[O:27][N:26]=[C:25]([C:28](=[O:29])[NH:34][CH3:33])[CH:24]=3)[CH2:13]1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 67607896Ethyl 5-[({[3-(6-fluoro-quinolin-2-yl)-3-azabicyclo[3.1.0]hex-6-yl]carbamoyl}oxy)-methyl]isoxazole-3-carboxylate

Product 1

HCID 131731960[3-(Methylcarbamoyl)isoxazol-5-yl]methyl [3-(6-fluoro-quinolin-2-yl)-3-azabicyclo[3.1.0]hex-6-yl]carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The procedure described in Example 6, step 6.4. is followed. Starting from 0.30 g (0.68 mmol) of ethyl 5-[({[3-(6-fluoro-quinolin-2-yl)-3-azabicyclo[3.1.0]hex-6-yl]carbamoyl}oxy)-methyl]isoxazole-3-carboxylate and 8.50 ml of an 8M solution of methylamine in ethanol, and after high-temperature crystallization in diethyl ether, 0.17 g (60%) of product is obtained in the form of a white solid.

Workup

  1. customafter high-temperature crystallization in diethyl ether

Sources & evidence

ORD record
ord-741d544af8a54d3fa8c0ee0acf46a048
Source dataset
uspto-grants-2014_10
Patent number
US08865738B2

Reaction notes

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