Cycloheptylamine → HCID 10223727, compound

HRID 1375490Notes

Reaction equation

HRID 1375490 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[F:10][C:11]1C=C(C=CC=1N)OC.CC[N:22]([CH:26]([CH3:28])[CH3:27])C(C)C.[CH:29]1([NH2:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][NH2:41].[C:43]([O:46][CH2:47][CH3:48])(=O)C>CC#N>[CH:29]1([NH:36][C:2]2[N:4]=[C:5]([NH:41][CH2:40][CH2:39][N:38]([CH3:42])[CH3:37])[N:7]=[C:8]([NH:22][C:26]3[CH:27]=[CH:48][C:47]([O:46][CH3:43])=[C:11]([F:10])[CH:28]=3)[N:1]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

8

Reactant 6

HCID 2899CycloheptylamineHCID 7954Cyanuric chlorideHCID 8857Ethyl AcetateHCID 66053N,N-DimethylethylenediamineHCID 81531Diisopropylethylamine3×HCID 37563832-Fluoro-4-methoxyaniline

Product 1

HCID 10223727HCID 10223727, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cyanuric chloride (1.84 g, 10 mmol) in CH3CN (20 mL) was cooled to about −10° C. was added 3-fluoro-p-anisidine (1.41 g, 10 mmol) followed by DIEA (1.8 mL, 10 mmol). The reaction was stirred for about 45 min then at room temperature for about 45 min under an N2 atmosphere. Cycloheptylamine (1.26 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the reaction was stirred at room temperature overnight. N,N-dimethylethylenediamine (1.1 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the mixture was heated at reflux under N2 overnight. The reaction was diluted with ethyl acetate, washed with brine, and dried over anhydrous K2CO3. The material (1.178 g) was purified by silica gel column chromatography to afford a solid 150 (1.178 g, 28%), mp 73–76° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 10.8 min, 95.1% purity; MS (ESI): m/z 418 (M+H, 100), 373 (11.9), 322 (7.8), 277 (6.8), 162 (3.6).

Workup

  1. waitat room temperature for about 45 min under an N2 atmosphere
  2. stirringthe reaction was stirred at room temperature overnight
  3. temperaturethe mixture was heated
  4. temperatureat reflux under N2 overnight
  5. washwashed with brine
  6. dry with materialdried over anhydrous K2CO3
  7. customThe material (1.178 g) was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ed79b5bb28e47fe9e5bc59dbadcd206
Source dataset
uspto-grants-2007_01
Patent number
US07169785B2

Reaction notes

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