Methyl 3-mercaptopropionate → Methyl 3-(5-(2-chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate

HRID 911786Notes

Reaction equation

HRID 911786 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.[SH:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]>>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:15][C:4]1[CH:3]=[C:2]([S:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:7]=[N:6][C:5]=1[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH3:14])[N:13]=1

Participants

3

Reactant 2

HCID 18050Methyl 3-mercaptopropionateHCID 24764526N-(5-bromo-3-(2-chlorophenylthio)pyridin-2-yl)-4-methylthiazol-2-amine

Product 1

HCID 24764616Methyl 3-(5-(2-chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate

Procedure

Prepared according to the method of Example 13 from N-(5-bromo-3-(2-chlorophenylthio)pyridin-2-yl)-4-methylthiazol-2-amine (prepared according to Example 47) and methyl 3-mercaptopropanoate. 1H NMR (CDCl3) δ 9.01 (bs, 1H), 8.52 (d, 1H), 7.95 (d, 1H), 7.40 (dd, 1H), 7.16-7.06 (m, 2H), 6.66 (dd, 1H), 6.46 (s, 1H), 3.68 (s, 3H), 3.07 (t, 2H), 2.61 (t, 2H), 2.32 (s, 3H); Mass spectrum (esi) m/z=452.1 (M+H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-537f53a8725c4863820249684842c6a9
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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