4-(Methylthio)benzaldehyde → [5-(3-Chloro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-pyridin-3-yl-amine

HRID 908163Notes

Reaction equation

HRID 908163 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=O.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH2:23])=[S:22])[CH:15]=1.[CH3:24][C:25]1N=C(NC2C=NC=CN=2)SC=1C1C=CC(SC)=CC=1.CSC1C=CC(C=O)=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[S:22][C:21]([NH:20][C:16]3[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=3)=[N:23][C:24]=2[CH3:25])[CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

5

Reactant 4

HCID 769854-(Methylthio)benzaldehydeHCID 27605153-PyridylthioureaHCID 117361153-Chloro-4-methanesulfonyl-benzaldehydeHCID 86761401[4-Methyl-5-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-pyrazin-2-yl-amine

Product 1

HCID 86606212[5-(3-Chloro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-pyridin-3-yl-amine

Procedure

The title compound is prepared starting from 3-chloro-4-methanesulfonyl-benzaldehyde (prepared as described in WO 01/49660 A1) and 3-pyridylthiourea following an analogous sequence of reactions described for the preparation of [4-Methyl-5-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-pyrazin-2-yl-amine (27c) from 4-methylsulfanyl-benzaldehyde.

Sources & evidence

ORD record
ord-5ee7a626977742408330c59e93a7a080
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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