HCID 58138998, compound → HCID 178476192, compound
Reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][CH2:10][OH:11])=[CH:4][C:3]=1[F:12].Cl.[O:14]=[CH:15][CH2:16][C:17](S)=[NH:18]>>[C:10]([O:11][CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([F:12])[C:2]([NH:1][C:17](=[NH:18])[CH2:16][C:15]([C:6]2[CH:5]=[CH:4][C:3]([F:12])=[CH:2][C:7]=2[F:8])=[O:14])=[C:7]([F:8])[CH:6]=1)(=[O:11])[CH3:9]Participants
3
Procedure
In stage 1, the 2-(4-Amino-3,5-difluorophenyl)ethanol and 4-Chlorophenyl difluorophenyl)-3-oxopropanimidothioate hydro-chloride are reacted together to form 2-(4-{[3-(2,4-Difluorophenyl)-3-oxopropanimidoyl]amino}-3,5-difluorophenyl)ethyl acetate. In stage 2, propiolic acid is added to form 2-{4-[6-Amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenyl}ethyl acetate. In stage 3, the acetate group is hydrolysed to leave an alcohol and in stage 4 the resulting alcohol group is oxidised to an aldehyde. The compound of the invention is then formed in stage 5, by the addition of tert-butyl L-alaninate hydrochloride. Tert-butyl L-alaninate hydrochloride is commercially available.
Sources & evidence
- ORD record
- ord-70847c112bb640438e7a55a65e5886ad
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388136B2
Reaction notes
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