methyl N-{[3'-(aminomethyl)biphenyl-4-yl]sulfonyl}valinate → methyl N-{[3'-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)biphenyl-4-yl]sulfonyl}valinate

HRID 606510Notes

Reaction equation

HRID 606510 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@H:19]([C:23]([O:25][CH3:26])=[O:24])[CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[O:27]=[C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30]([C:38](OCC)=[O:39])[NH:29]1>CCO>[O:27]=[C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30]([C:38]([NH:1][CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[CH:10]=[CH:11][C:12]([S:15]([NH:18][C@H:19]([C:23]([O:25][CH3:26])=[O:24])[CH:20]([CH3:21])[CH3:22])(=[O:17])=[O:16])=[CH:13][CH:14]=3)[CH:6]=[CH:7][CH:8]=2)=[O:39])[NH:29]1

Participants

4

Reactant 2

HCID 66769176methyl N-{[3'-(aminomethyl)biphenyl-4-yl]sulfonyl}valinateHCID 135437466Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 136380956methyl N-{[3'-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)biphenyl-4-yl]sulfonyl}valinateYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of methyl N-{[3′-(aminomethyl)biphenyl-4-yl]sulfonyl}valinate obtained in Reference Example 94 (0.300 g, 0.797 mmol) and ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate obtained according to the methods described in Journal of Organic Chemistry (1978), 43(23), 4485-7 and the like (0.145 g, 0.664 mmol) in EtOH (9 mL) was stirred at 90° C. for 5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with 0.1N hydrochloric acid and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound as a colorless oil (0.375 g, 86%).

Workup

  1. customobtained
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with 0.1N hydrochloric acid and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-20fd0b7cbf434761998286b24d3a289d
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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