HCID 67353879, compound → 3-{3-Fluoro-4-[3-(4-fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carboxylic acid

HRID 75796Notes

Reaction equation

HRID 75796 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:19])=[C:13]([F:28])[CH:12]=2)[CH:7]=1)=[O:5])C.C1(NC(=O)NC2C=CC(C3C=C(C(O)=O)ON=3)=CC=2)C=CC=CC=1>>[F:28][C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[O:10][N:9]=2)[CH:16]=[CH:15][C:14]=1[NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:19]

Participants

3

Reactant 2

HCID 67353879HCID 67353879, compoundHCID 673550113-[4-(3-Phenyl-ureido)-phenyl]-isoxazole-5-carboxylic acid

Product 1

HCID 673527213-{3-Fluoro-4-[3-(4-fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carboxylic acidYield 89%

Procedure

The title compound was prepared from 3-{3-fluoro-4-[3-(4-fluoro-phenyl)-ureido]-phenyl}-isoxazole-5-carboxylic acid ethyl ester by using the procedure as described for the preparation of 3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carboxylic acid (Example 76, step 2) and was obtained in 89% yield; MS (m/z): 360 (M++1); 1H NMR (DMSO-d6) δ: 7.13 (t, 2H), 7.46 (m, 2H), 7.76 (m, 2H), 7.84 (m, 1H), 8.32 (t, 1H), 8.78, 9.18 (2×s, 2H, 2×NH).

Workup

  1. customwas obtained in 89% yield

Sources & evidence

ORD record
ord-b4376a868f4e4733aea4d77c0326feec
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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