L-Valine → HCID 13881847, compound

HRID 979481Notes

Reaction equation

HRID 979481 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH2:22])[CH2:17][CH2:16]1.C(N(CC)CC)C.[C:30](=[S:32])=S.CI.[NH2:35][C@H:36]([C:40](O)=[O:41])[CH:37]([CH3:39])[CH3:38]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][N:22]2[C:40](=[O:41])[CH:36]([CH:37]([CH3:39])[CH3:38])[NH:35][C:30]2=[S:32])[CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 6287L-ValineHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471Triethylamine2×HCID 138818461-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinemethanamine

Product 1

HCID 13881847HCID 13881847, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6,7-dimethoxy-4-[4-(aminomethyl)-piperidino] quinazoline (302 mg; 1 mmol), triethylamine (0.14 ml; 1 mmol), carbon disulfide (66 mcl; 1 mmol) and ethanol (3 ml) was stirred at room temperature for 2 hours. After addition of methyl iodide (62 mcl; 1 mmol), the mixture was further stirred for 1 hour. After addition of L-valine (351 mg; 3 mmol) and triethylamine (0.42 ml, 3 mmol), the reaction solution was refluxed for 10 hours. The resultant reaction solution was left at room temperature for 12 hours to precipitate crystals which were then recovered by filtration. The crystals were successively washed with an aqueous solution of 10% NaHCO3, water and ethanol and dried. The dried material was recrystallized by using a mixture of chloroform and ethanol to yield the desired product (188.6 mg; 41.1%).

Workup

  1. stirringthe mixture was further stirred for 1 hour
  2. temperaturethe reaction solution was refluxed for 10 hours
  3. customThe resultant reaction solution
  4. waitwas left at room temperature for 12 hours
  5. customto precipitate crystals which
  6. filtrationwere then recovered by filtration
  7. washThe crystals were successively washed with an aqueous solution of 10% NaHCO3, water and ethanol
  8. customdried
  9. customThe dried material was recrystallized
  10. additiona mixture of chloroform and ethanol

Sources & evidence

ORD record
ord-738960b201a746f0903ab5189f61922e
Source dataset
uspto-grants-1987_05
Patent number
US04668683

Reaction notes

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