Triethylamine → N-(2-isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-yl)-2-(6-trifluoromethylquinazolin-4-ylamino)acetamide

HRID 130382Notes

Reaction equation

HRID 130382 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH:6]1[CH2:16][CH:9]2[CH2:10][N:11]([CH:13]([CH3:15])[CH3:14])[CH2:12][CH:8]2[CH:7]1[CH2:17][O:18][CH3:19])=[O:4].Cl[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=2)[N:24]=[CH:23][N:22]=1.C(N(CC)CC)C>C(O)C>[CH:13]([N:11]1[CH2:12][CH:8]2[CH:7]([CH2:17][O:18][CH3:19])[CH:6]([NH:5][C:3](=[O:4])[CH2:2][NH:1][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:31]([F:33])([F:34])[F:32])[CH:29]=4)[N:24]=[CH:23][N:22]=3)[CH2:16][CH:9]2[CH2:10]1)([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 210750954-Chloro-6-(trifluoromethyl)quinazolineHCID 692215432-amino-N-(2-isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-yl)acetamide

Product 1

HCID 69224927N-(2-isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-yl)-2-(6-trifluoromethylquinazolin-4-ylamino)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-N-(2-isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-yl)acetamide, 4-chloro-6-trifluoromethylquinazoline (see Armarego et al., J. Chem. Soc. B, 1967, 449) and triethylamine in ethanol is heated at reflux until the reaction is complete. The solution is concentrated under vacuum yielding a residue. The residue is purified by reverse phase HPLC and lyophilization providing the title product.

Workup

  1. temperatureis heated
  2. temperatureat reflux until the reaction
  3. concentrationThe solution is concentrated under vacuum
  4. customyielding a residue
  5. customThe residue is purified by reverse phase HPLC and lyophilization

Sources & evidence

ORD record
ord-9e161f22675b48dda1bbf83ba3010999
Source dataset
uspto-grants-2008_06
Patent number
US07381738B2

Reaction notes

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