Ethanol → HCID 87618288, compound

HRID 2111394Notes

Reaction equation

HRID 2111394 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][CH2:13][CH:12]1[CH3:16])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][CH2:13][CH:12]3[CH3:16])[C:17]=2[N:18]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 87618835HCID 87618835, compound

Product 1

HCID 87618288HCID 87618288, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 50 mL of ethanol, 1 mL of acetic acid and 2.5 g of the (rac)-3-[(5-amino-2-chloro-pyrimidin-4-yl)-(2-methyl-cyclopentyl)-amino]-propanoic acid ethyl ester (V-57) 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. Trituration of the residue with ether, provided 1.6 g of (rac)-2-chloro-9-(2-methyl-cyclopentyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-57).

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

Sources & evidence

ORD record
ord-8ee4393416d446afa133d4ddfb375c9f
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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