Isoxazole-5-carbonyl chloride → HCID 22478409, compound

HRID 2184678Notes

Reaction equation

HRID 2184678 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=1.[O:21]1[C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=[N:22]1>>[ClH:20].[Cl:20][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[F:19])[NH:12][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:26]([C:25]3[O:21][N:22]=[CH:23][CH:24]=3)=[O:27])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 2736707Isoxazole-5-carbonyl chlorideHCID 108807516-Amino-4-(3-chloro-4-fluoroanilino)quinazoline

Product 1

HCID 22478409HCID 22478409, compoundYield 87%

Procedure

Using an analogous procedure to that described in Example 18, 6-amino-4-(3-chloro-4-fluoroanilino)quinazoline was reacted with 5-isoxazolecarbonyl chloride to give 4-(3-chloro-4-fluoroanilino)-6-(isoxazole-5-carboxamido)quinazoline hydrochloride salt in 87% yield, m.p. >250° C.; NMR Spectrum: 7.4 (d, 1H), 7.5 (t, 1H), 7.65 (m, 2H), 8.0 (m, 2H), 8.85 (d, 1H), 8.9 (s, 1H), 11.4 (s, 1H); Elemental Analysis: Found C, 50.8; H, 3.3; N, 16.3; C18H11ClFN5O2 1HCl 0.4H2O 0.24DMA requires C, 50.8; H, 3.4; N, 16.4%.

Sources & evidence

ORD record
ord-c9f7169fcf4743af9d684ffca9954d8e
Source dataset
uspto-grants-2002_06
Patent number
US06399602B1

Reaction notes

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