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Acetic Acid → (+/-)-2-[4-(4-Amino-quinazolin-7-ylmethyl)-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl]-5-chloro-indole-1-carboxylic acid tert-butyl ester

HRID 1433012
Notes
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Reaction equation

HRID 1433012 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:18][N:19]1[CH2:24][C:23](=[O:25])[N:22]([CH2:26][C:27]2[CH:32]=C[C:30](C#N)=[C:29](N)[CH:28]=2)[CH:21]([C:36]([O:38][CH3:39])=[O:37])[CH2:20]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:40]1[CH:45]=[N:44][CH:43]=[N:42][CH:41]=1.CC(O)=O>CCO>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:18][N:19]1[CH2:24][C:23](=[O:25])[N:22]([CH2:26][C:27]2[CH:32]=[C:41]3[C:30]([C:45]([NH2:40])=[N:44][CH:43]=[N:42]3)=[CH:29][CH:28]=2)[CH:21]([C:36]([O:38][CH3:39])=[O:37])[CH2:20]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 92621,3,5-Triazine2×HCID 54288444(+/-)-2-[4-(3-Amino-4-cyano-benzyl)-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl]-5-chloro-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 53785442(+/-)-2-[4-(4-Amino-quinazolin-7-ylmethyl)-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl]-5-chloro-indole-1-carboxylic acid tert-butyl esterYield 24.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing (±)-2-[4-(3-amino-4-cyano-benzyl)-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl]-5-chloro-indole-1-carboxylic acid tert-butyl ester (100 mg, 0.18 mmol), 1,3,5-triazine (146 mg, 1.81 mmol), and glacial HOAc (99 mg, 1.81 mmol) in absolute EtOH (10 mL) is maintained at reflux for 16 hours. A second portion of 1,3,5-triazine (146 mg, 1.81 mmol) and glacial HOAc (99 mg, 1.81 mmol) is added and the reaction mixture is maintained at reflux for an additional 16 hours. The reaction mixture is concentrated in vacuo and the crude product is diluted with water/CH3CN and purified by reverse-phase HPLC [Buffer A: water w/0.1% TFA; Buffer B: CH3CN w/0.1% TFA; Gradient: 0% B to 60% B over 30 min] to provide 26 mg (20%) of the title compound as a white solid which is used directly in the next reaction without further characterization.

Workup

  1. temperatureis maintained
  2. temperatureat reflux for 16 hours
  3. temperaturethe reaction mixture is maintained
  4. temperatureat reflux for an additional 16 hours
  5. concentrationThe reaction mixture is concentrated in vacuo
  6. additionthe crude product is diluted with water/CH3CN
  7. custompurified by reverse-phase HPLC [Buffer A: water

Sources & evidence

ORD record
ord-cee5dbd33fd143108fdaeb94cacefb81
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