3-Isoxazolamine → 3-[6-(4-(2-methoxyethyl)piperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]-N-isoxazol-3-yl-4-methylbenzamide

HRID 641955Notes

Reaction equation

HRID 641955 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N:22]3[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][O:30][CH3:31])[CH2:24][CH2:23]3)[CH:18]=2)[N:13]=[CH:12]1.[NH2:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1>>[CH3:31][O:30][CH2:29][CH2:28][N:25]1[CH2:26][CH2:27][N:22]([C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][N:11]([C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=2[CH3:1])[C:6]([NH:32][C:33]2[CH:37]=[CH:36][O:35][N:34]=2)=[O:7])[C:20]3=[O:21])[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 18102163-IsoxazolamineHCID 686032744-methyl-3-[6-(4-(2-methoxyethyl)piperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid

Product 1

HCID 119968613-[6-(4-(2-methoxyethyl)piperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]-N-isoxazol-3-yl-4-methylbenzamide

Procedure

Using an analogous procedure to that described paragraph (A) in the portion of Example 4, 4-methyl-3-[6-(4-(2-methoxyethyl)piperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid was reacted with 3-aminoisoxazole to give 3-[6-(4-(2-methoxyethyl)piperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]-N-isoxazol-3-yl-4-methylbenzamide; NMR Spectrum: (DMSOd6) 2.18 (s, 3H), 2.58 (m, 6H), 3.26 (m, 7H), 3.47 (t, 2H), 7.05 (s, 1H), 7.50 (s, 1H), 7.66 (m, 3H), 8.10 (m, 2H), 8.13 (s, 1H), 8.87 (s, 1H), 11.48 (s, 1H); Mass Spectrum: M+H+ 489.

Sources & evidence

ORD record
ord-420e1dd22b7747ff8748171363f7fe7e
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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