1-(4-(6-(4-Methoxybenzylamino)pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea → 1-(4-(2-Carbamoylpyridin-4-yloxy)-3,5-difluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea

HRID 2374072Notes

Reaction equation

HRID 2374072 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([F:18])[C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH2:15])=[O:14])[CH:8]=2)=[C:4]([F:19])[CH:3]=1.COC1C=CC(CNC2N=CN=C(OC3C=CC(N[C:42]([NH:44][C:45](=[O:54])[CH2:46][C:47]4[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=4)=[O:43])=CC=3F)C=2)=CC=1>>[C:13]([C:9]1[CH:8]=[C:7]([O:6][C:5]2[C:16]([F:18])=[CH:17][C:2]([NH:1][C:42]([NH:44][C:45](=[O:54])[CH2:46][C:47]3[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=3)=[O:43])=[CH:3][C:4]=2[F:19])[CH:12]=[CH:11][N:10]=1)(=[O:14])[NH2:15]

Participants

3

Reactant 2

HCID 115698931-(4-(6-(4-Methoxybenzylamino)pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)ureaHCID 598528534-(4-Amino-2,6-difluorophenoxy)picolinamide

Product 1

HCID 598528821-(4-(2-Carbamoylpyridin-4-yloxy)-3,5-difluorophenyl)-3-(2-(4-fluorophenyl)acetyl)ureaYield 52%

Procedure

4-(4-Amino-2,6-difluorophenoxy)picolinamide (104 mg, 0.39 mmol) was converted to the title compound (91 mg, 52%) in a manner similar to the preparation of Compound D of Example 112. 1H NMR (DMSO-d6) δ 11.07 (s, 1H), 10.62 (s, 1H), 8.50 (d, 1H, J=5.6 Hz), 8.11 (br s, 1H), 7.72 (br s, 1H), 7.61 (m, 2H), 7.36-7.37 (d, 1H, J=2.3 Hz), 7.23-7.31 (m, 3H), 7.11 (m, 2H), 3.69 (s, 2H); HRMS(ESI+), 445.1124 (M+H)+ calcd., 445.1117 (M+H)+ found.

Sources & evidence

ORD record
ord-7de5cf040a1c4727935dfaa7384d0312
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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