2-(Benzylamino)-2-oxoacetic acid → 4-(4-(2-(Benzylamino)-2-oxoacetamido)-2-fluorophenoxy)picolinamide

HRID 2377736Notes

Reaction equation

HRID 2377736 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][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:18])[CH:3]=1.[CH2:19]([NH:26][C:27](=[O:31])[C:28](O)=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([NH:26][C:27](=[O:31])[C:28]([NH:1][C:2]1[CH:17]=[CH:16][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:18])[CH:3]=1)=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 2426432-(Benzylamino)-2-oxoacetic acidHCID 231532054-(4-Amino-2-fluorophenoxy)picolinamide

Product 1

HCID 587326274-(4-(2-(Benzylamino)-2-oxoacetamido)-2-fluorophenoxy)picolinamideYield 90%

Procedure

The coupling of 4-(4-amino-2-fluorophenoxy)picolinamide to 2-(benzylamino)-2-oxoacetic acid was carried out in a manner similar to that which is described in Step C of Example 1 to give the title compound (90%) as a tan solid. 1H NMR (DMSO-d6) δ 11.08 (s, 1H), 9.63 (t, 1H, J=6 Hz), 8.56 (d, 1H, J=5.6 Hz), 8.15 (br s, 1H), 8.02 (dd, 1H, J=12.8, 2 Hz), 7.82 (d, 1H, J=9.2 Hz), 7.75 (br s, 1H), 7.47 (t, 1H, J=8.8 Hz), 7.39-7.23 (m, 7H), 4.41 (d, 2H, J=6.4 Hz); MS(ESI+) m/z 409.22 (M+H)+.

Sources & evidence

ORD record
ord-f95e40dbff9446dea03be4b7a3d34a80
Source dataset
uspto-grants-2008_12
Patent number
US07470693B2

Reaction notes

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