Cyclohexylamine → HCID 58999039, compound

HRID 2105781Notes

Reaction equation

HRID 2105781 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.C[O:13][C:14]([C:16]1[C:20]([CH3:21])=[C:19]([C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[N:18]([CH2:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[C:17]=1[CH3:43])=O>C1(C)C=CC=CC=1>[CH:1]1([NH:7][C:14]([C:16]2[C:20]([CH3:21])=[C:19]([C:22]3[CH:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=3)[N:18]([CH2:36][CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]3)[C:17]=2[CH3:43])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 16682925TrimethylaluminumHCID 86594074HCID 86594074, compound

Product 1

HCID 58999039HCID 58999039, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 59.5 μl (0.52 mmol) of cyclohexylamine in toluene (2 ml) was treated at RT dropwise with 0.26 μl of a 2 M solution of trimethylaluminum in toluene (0.52 mmol). The reaction solution was stirred 1 h at RT, 200 mg (0.43 mmol) of 5-(3,5-bis-trifluoromethyl-phenyl)-1-cyclohexylmethyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester in toluene (2 ml) were added and reaction mixture was heated at 110° C. for 3 h. The mixture was then partitioned between water and ethyl acetate, the organic layer was isolated, dried over sodium sulfate and concentrated in vacuo and purified by column chromatography to give 114 mg of the title compound, MS (ISP) 529.3 (M+H)+.

Workup

  1. customreaction mixture
  2. temperaturewas heated at 110° C. for 3 h
  3. customThe mixture was then partitioned between water and ethyl acetate
  4. customthe organic layer was isolated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-13fa80e50bfa4dc2a65574192d2ada59
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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