Diisopropylethylamine → 4-oxo-N-({3-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}propyl)oxy]phenyl}methyl)-3,4-dihydroquinazoline-2-carboxamide

HRID 606506Notes

Reaction equation

HRID 606506 reaction equation
[C:1]1([C:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH:12]=[N:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:19]=[C:20]([CH2:24][NH2:25])[CH:21]=[CH:22][CH:23]=3)=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:38]=[C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:42]=[C:41]([C:49](OCC)=[O:50])[NH:40]1.C(N(CC)C(C)C)(C)C>CCO>[O:38]=[C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:42]=[C:41]([C:49]([NH:25][CH2:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH2:16][CH2:15][CH2:14][O:13][C:10]3[N:11]=[CH:12][N:8]([C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:9]=3)[CH:19]=2)=[O:50])[NH:40]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66768833HCID 66768833, compoundHCID 135437466Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 1363809674-oxo-N-({3-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}propyl)oxy]phenyl}methyl)-3,4-dihydroquinazoline-2-carboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1-{3-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}propyl)oxy]phenyl}methanamine obtained in Reference Example 85 (0.300 g, 0.611 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 (0.133 g, 0.611 mmol) and N,N-diisopropylethylamine (0.213 mL, 1.22 mmol) in EtOH (4.5 mL) was stirred under microwave irradiation at 100° C. for 1.5 hr (Discover (trademark; CEM Corp), 50 W, run time: 5 min, hold time: 1.5 hr). After the reaction mixture was allowed to cool to room temperature, the precipitated solid was collected by filtration, and washed with EtOH to give the title compound as a white powder (0.315 g, 78%).

Workup

  1. customobtained
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with EtOH

Sources & evidence

ORD record
ord-d0f06b0a03d749428eb856d50c348f7d
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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