[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetic acid → 4-chloro-N-(4-(2-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenylamino)-2-oxoethyl)thiazol-2-yl)benzamide

HRID 901003Notes

Reaction equation

HRID 901003 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([OH:17])=O)[N:13]=2)=[O:7])=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=[O:33])=[CH:23][C:22]=1[F:34]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15](=[O:17])[NH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]4=[O:33])=[CH:23][C:22]=3[F:34])[N:13]=2)=[O:7])=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 677042[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetic acidHCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-one

Product 1

HCID 426430704-chloro-N-(4-(2-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenylamino)-2-oxoethyl)thiazol-2-yl)benzamide

Procedure

In analogy to example 1.3, [2-(4-chloro-benzoylamino)-thiazol-4-yl]-acetic acid (example 1.2) was coupled with 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (CAS 536747-52-1, prepared according to C. F. Bigge et al., patent application WO 2003045912) to give 4-chloro-N-(4-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-methyl}-thiazol-2-yl)-benzamide, using general procedure B. Off-white solid. MS 483.3 ([M+H]+)

Sources & evidence

ORD record
ord-09a946103a724f09b749d39bc25c07ab
Source dataset
uspto-grants-2008_04
Patent number
US07361672B2

Reaction notes

Loading…