Diethyl Ether → HCID 178505901, compound

HRID 406294Notes

Reaction equation

HRID 406294 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C@H:9]2[CH2:12][C@H:11]([NH:13][CH2:14][C:15]3[C:16]4[N:17]([CH:21]=[CH:22][N:23]=4)[CH:18]=[CH:19][CH:20]=3)[CH2:10]2)=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]\[C:31]([OH:33])=[O:32].C(OCC)C>CO>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]\[C:31]([OH:33])=[O:32].[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C@H:9]2[CH2:12][C@H:11]([NH:13][CH2:14][C:15]3[C:16]4[N:17]([CH:21]=[CH:22][N:23]=4)[CH:18]=[CH:19][CH:20]=3)[CH2:10]2)=[CH:4][C:3]=1[C:24]([F:26])([F:25])[F:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 444266Maleic AcidHCID 178505899HCID 178505899, compound

Product 1

HCID 178505901HCID 178505901, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

trans-3-{[4-Fluoro-3-(trifluoromethyl)phenyl]oxy}-N-(imidazo[1,2-a]pyridin-8-ylmethyl)cyclobutanamine (1035 mg, 2.73 mmol) and maleic acid (317 mg, 2.73 mmol) were dissolved in methanol (20 mL) and the solution stirred for 30 minutes. It was then concentrated in vacuo to give an orange gum. Diethyl ether was added to this residue to precipitate out the salt as a solid. The ether was removed in vacuo to give the title compound as a pale orange solid (1.299 g, 2.62 mmol).

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customto give an orange gum
  3. customto precipitate out the salt as a solid
  4. customThe ether was removed in vacuo

Sources & evidence

ORD record
ord-af33d38ef8af4e34b4926d98a1bcab24
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

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