Thiazole → HCID 178433123, compound

HRID 908181Notes

Reaction equation

HRID 908181 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH3:10])=[CH:4][C:3]=1[S:12]([NH:15][CH2:16][CH2:17][OH:18])(=[O:14])=[O:13].S1C=CN=C1.ClC1C=CC(CC(=O)C)=CC=1S(N)(=O)=O.ClC1C=CC(C2SC(NC3C=NC=CN=3)=NC=2C)=CC=1S(N)(=O)=O.[NH:63]1[CH:67]=[CH:66][C:65]([NH:68][C:69]([NH2:71])=[S:70])=[N:64]1>>[OH:18][CH2:17][CH2:16][NH:15][S:12]([C:3]1[CH:2]=[CH:7][CH:6]=[C:5]([C:8]2[S:70][C:69]([NH:68][C:65]3[CH:66]=[CH:67][NH:63][N:64]=3)=[N:71][C:9]=2[CH3:10])[CH:4]=1)(=[O:14])=[O:13]

Participants

6

Reactant 5

HCID 9256ThiazoleHCID 673909962-Chloro-N-(2-hydroxy-ethyl)-5-(2-oxo-propyl)-benzenesulfonamideHCID 673923132-Chloro-5-(2-oxo-propyl)-benzenesulfonamideHCID 86606216HCID 86606216, compoundHCID 178514162HCID 178514162, compound

Product 1

HCID 178433123HCID 178433123, compound

Procedure

The titled compound was prepared from N-(2-hydroxy-ethyl)-3-(2-oxo-propyl)-benzenesulfonamide (43b) following the two-step procedure (bromination, thiazole formation) described for the conversion of 2-chloro-5-(2-oxo-propyl)-benzene-sulfonamide (33a) to 2-chloro-5-[4-methyl-2-(pyrazin-2-ylamino)-thiazol-5-yl]-benzenesulfonamide (33c) replacing pyrazin-2-yl-thiourea (1a) in the final step with (1H-pyrazol-3-yl)-thiourea (35a).

Sources & evidence

ORD record
ord-81bae09f512e4f77a5242aca15becc2a
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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