3-Isoxazolamine → 3-[8-cyano-6-(4-ethylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]-N-isoxazol-3-yl-4-methylbenzamide

HRID 641970Notes

Reaction equation

HRID 641970 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH3:31])[CH2:26][CH2:25]2)[CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][N:9]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:16](O)=[O:17])[C:8]2=[O:23])#[N:2].[NH2:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1>>[C:1]([C:3]1[CH:4]=[C:5]([N:24]2[CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH2:29]2)[CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][N:9]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:16]([NH:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1)=[O:17])[C:8]2=[O:23])#[N:2]

Participants

3

Reactant 2

HCID 18102163-IsoxazolamineHCID 686041843-[8-cyano-6-(4-ethylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoic acid

Product 1

HCID 119970143-[8-cyano-6-(4-ethylpiperazin-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, 3-[8-cyano-6-(4-ethylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoic acid was reacted with 3-aminoisoxazole to give 3-[8-cyano-6-(4-ethylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]-N-isoxazol-3-yl-4-methylbenzamide; NMR Spectrum: (DMSOd6) 1.03 (t, 3H), 2.19 (s, 3H), 2.38 (q, 2H), 2.53 (m, 4H), 3.35 (m, 4H), 7.04 (s, 1H), 7.60 (d, 1H), 7.69 (s, 1H), 8.10 (m, 3H), 8.29 (s, 1H), 8.84 (s, 1H), 11.47 (s, 1H); Mass Spectrum: M+H+ 484.

Sources & evidence

ORD record
ord-eacd0aad49ee49ad9fd25000a9bbedcd
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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