Triethylamine → 4-Oxo-N-((4'-((((5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl)sulfonyl)methyl)biphenyl-3-yl)methyl)-3,4-dihydroquinazoline-2-carboxamide

HRID 606433Notes

Reaction equation

HRID 606433 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][S:16]([CH2:19][C:20]3[NH:21][C:22](=[O:25])[NH:23][N:24]=3)(=[O:18])=[O:17])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[O:26]=[C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=[C:29]([C:37](OCC)=[O:38])[NH:28]1.C(N(CC)CC)C.CC(N(C)C)=O>CCO.C(OCC)(=O)C>[O:26]=[C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=[C:29]([C:37]([NH:1][CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[CH:14]=[CH:13][C:12]([CH2:15][S:16]([CH2:19][C:20]4[NH:21][C:22](=[O:25])[NH:23][N:24]=4)(=[O:17])=[O:18])=[CH:11][CH:10]=3)[CH:6]=[CH:7][CH:8]=2)=[O:38])[NH:28]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 135437466Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylateHCID 1360544705-[({[3'-(aminomethyl)biphenyl-4-yl]methyl}sulfonyl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 1360544874-Oxo-N-((4'-((((5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl)sulfonyl)methyl)biphenyl-3-yl)methyl)-3,4-dihydroquinazoline-2-carboxamideYield 55%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-[({[3′-(aminomethyl)biphenyl-4-yl]methyl}sulfonyl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one obtained in Reference Example 111 (0.060 g, 0.167 mmol), 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 (0.024 g, 0.112 mmol) and triethylamine (0.389 mL, 1.12 mmol) in EtOH (3 mL)-DMA (3 mL) was stirred at 90° C. for 24 hr. The reaction mixture 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, and the residue was crystallized from EtOH-diethyl ether to give the title compound as a pale-yellow powder (0.032 g, 55%).

Workup

  1. customobtained
  2. washwashed with 0.1N hydrochloric acid and saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was crystallized from EtOH-diethyl ether

Sources & evidence

ORD record
ord-2344f62c362b4664ba4ddf5775acdd18
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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