Methylamine → 3-(Methylcarbamoyl)isoxazol-5-ylmethyl 2-(6-fluoroquinolin-2-yl)-2-azaspiro[3.3]hept-6-ylcarbamate

HRID 336547Notes

Reaction equation

HRID 336547 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[CH2:15][C:14]3([CH2:18][CH:17]([NH:19][C:20]([O:22][CH2:23][C:24]4[O:28][N:27]=[C:26]([C:29](OCC)=[O:30])[CH:25]=4)=[O:21])[CH2:16]3)[CH2:13]1)[CH:6]=[CH:5]2.[CH3:34][NH2:35]>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[CH2:13][C:14]3([CH2:16][CH:17]([NH:19][C:20](=[O:21])[O:22][CH2:23][C:24]4[O:28][N:27]=[C:26]([C:29](=[O:30])[NH:35][CH3:34])[CH:25]=4)[CH2:18]3)[CH2:15]1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68000144Ethyl 5-[2-(6-Fluoroquinolin-2-yl)-2-azaspiro[3.3]hept-6-ylcarbamoyloxymethyl]isoxazole-3-carboxylate

Product 1

HCID 468509783-(Methylcarbamoyl)isoxazol-5-ylmethyl 2-(6-fluoroquinolin-2-yl)-2-azaspiro[3.3]hept-6-ylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a sealed tube, a solution of 0.130 g (0.28 mmol) of ethyl 5-[2-(6-fluoroquinolin-2-yl)-2-azaspiro[3.3]hept-6-ylcarbamoyloxymethyl]isoxazole-3-carboxylate, prepared in step 11.9., in 4.13 mL (28.01 mmol) of a solution (8M) of methylamine in ethanol, is stirred at room temperature for 5 hours. The mixture is evaporated to dryness. The residue obtained is crystallized from hot ether. The precipitate thus formed is filtered off and rinsed thoroughly with ether. After drying under vacuum at about 60° C., 0.05 g of pure product is obtained in the form of a white powder.

Workup

  1. customThe mixture is evaporated to dryness
  2. customThe residue obtained
  3. customis crystallized from hot ether
  4. customThe precipitate thus formed
  5. filtrationis filtered off
  6. washrinsed thoroughly with ether
  7. customAfter drying under vacuum at about 60° C.

Sources & evidence

ORD record
ord-d09addc233e64d72b63854c2ec3ac812
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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