Ethanol → HCID 87617704, compound

HRID 2111400Notes

Reaction equation

HRID 2111400 reaction equation
C(O)C.C([O:6][C:7](=O)[CH2:8][CH2:9][N:10]([C:17]1[C:22]([NH2:23])=[CH:21][N:20]=[C:19]([Cl:24])[N:18]=1)[CH:11]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12]1)C>C(O)(=O)C>[Cl:24][C:19]1[N:20]=[CH:21][C:22]2[NH:23][C:7](=[O:6])[CH2:8][CH2:9][N:10]([CH:11]3[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12]3)[C:17]=2[N:18]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 87617669HCID 87617669, compound

Product 1

HCID 87617704HCID 87617704, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 50 mL of ethanol, 1 mL of acetic acid and 2.6 g of the (rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-(3-methyl-cyclopentyl)-amino]-propanoic acid ethyl ester (V-58) prepared in the previous step was heated at reflux overnight, and then concentrated under reduced pressure. The residue was taken up in dichloromethane and washed successively with 10% sodium bicarbonate solution, and then water and dried over anhydrous sodium sulfate. The mixture was filtered and then concentrated under reduced pressure to the crude product. Trituration of the residue with ether, provided 1.8 g of (rac)-2-chloro-9-(3-methyl-cyclopentyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-58).

Workup

  1. customprepared in the previous step
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. concentrationconcentrated under reduced pressure
  5. washwashed successively with 10% sodium bicarbonate solution
  6. dry with materialwater and dried over anhydrous sodium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated under reduced pressure to the crude product

Sources & evidence

ORD record
ord-5ff520f2098f46c6ae92ae57c4922350
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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