1-{3-[(2-([1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy)ethyl)oxy}phenyl]methanamine → 5,6-difluoro-4-oxo-N-({3-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}ethyl)oxy]phenyl}methyl)-3,4-dihydroquinazoline-2-carboxamide

HRID 606403Notes

Reaction equation

HRID 606403 reaction equation
[C:1]1([C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:8]2[CH:12]=[N:11][C:10]([O:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]([CH2:23][NH2:24])[CH:20]=[CH:21][CH:22]=3)=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:37][C:38]1[C:47]([F:48])=[CH:46][CH:45]=[C:44]2[C:39]=1[C:40](=[O:54])[NH:41][C:42]([C:49](OCC)=[O:50])=[N:43]2>C(O)C>[F:37][C:38]1[C:47]([F:48])=[CH:46][CH:45]=[C:44]2[C:39]=1[C:40](=[O:54])[NH:41][C:42]([C:49]([NH:24][CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([O: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:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:9]=3)[CH:18]=1)=[O:50])=[N:43]2

Participants

4

Reactant 2

HCID 667690991-{3-[(2-([1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy)ethyl)oxy}phenyl]methanamineHCID 136029322Ethyl 5,6-difluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 1363809705,6-difluoro-4-oxo-N-({3-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}ethyl)oxy]phenyl}methyl)-3,4-dihydroquinazoline-2-carboxamideYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-{3-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy]ethyl)oxy}phenyl}methanamine obtained in Reference Example 32 (300 mg, 1.18 mmol) and ethyl 5,6-difluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate obtained in Reference Example 57 (562 mg, 1.18 mmol) in ethanol (10 mL) was stirred at 80° C. for 12 hr. The insoluble material was filtered off hot, and the filtrate was allowed to cool to room temperature. The precipitated solid was collected by filtration using glass filter, and the obtained solid was washed with diethyl ether to give 5,6-difluoro-4-oxo-N-({3-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}ethyl)oxy]phenyl}methyl)-3,4-dihydroquinazoline-2-carboxamide as a pale-yellow powder (330 mg, 41%).

Workup

  1. filtrationThe insoluble material was filtered off hot
  2. temperatureto cool to room temperature
  3. filtrationThe precipitated solid was collected by filtration
  4. filtrationfilter
  5. washthe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-6155de3ef4504fd9a218d806ba86b3aa
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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