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Acetic Acid → (2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 1432929
Notes
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Reaction equation

HRID 1432929 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[N:9][CH:8]=[N:7][CH:6]=1.[CH2:11]([O:18][C:19]([N:21]1[CH:26]([CH3:27])[CH2:25][N:24]([CH2:28][C:29]2[CH:34]=C[C:32](C#N)=[C:31](N)[CH:30]=2)[C:23](=[O:38])[C@@H:22]1[CH3:39])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>C(O)C>[CH2:11]([O:18][C:19]([N:21]1[CH:26]([CH3:27])[CH2:25][N:24]([CH2:28][C:29]2[CH:34]=[C:6]3[C:32]([C:10]([NH2:5])=[N:9][CH:8]=[N:7]3)=[CH:31][CH:30]=2)[C:23](=[O:38])[C@@H:22]1[CH3:39])=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 92621,3,5-TriazineHCID 57054342(2S,6RS)-4-(3-amino-4-cyano-benzyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 57166330(2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl esterYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Glacial acetic acid (0.9 ml, 15.54 mmol) and 1,3,5-triazine (840 mg, 10.36 mmol) is added to a solution of (2S,6RS)-4-(3-amino-4-cyano-benzyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (2.03 g, 5.18 mmol) in ethanol. The resulting mixture is heated to reflux overnight. Replaced the ethanol with ethyl acetate and washed with saturated sodium bicarbonate (5 mL). The ethyl acetate layer is dried with magnesium sulfate, filtered and condensed. The resulting residue is purified by flash colunm (SiO2, 20% methanol/methylene chloride) to give the product (2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (1.85 g, 85%) as a yellow solid. C23H25N5O3 MS m/z: 420.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux overnight
  3. washwashed with saturated sodium bicarbonate (5 mL)
  4. dry with materialThe ethyl acetate layer is dried with magnesium sulfate
  5. filtrationfiltered
  6. customcondensed
  7. customThe resulting residue is purified by flash colunm (SiO2, 20% methanol/methylene chloride)

Sources & evidence

ORD record
ord-5d393f2a70f241ca989619526d6e0e9f
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612075B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes