2-(1-Bromoethyl)pyridine → N-(3-(2-chlorophenylthio)-5-(1-(pyridin-2-yl)ethylthio)pyridin-2-yl)-4-methylthiazol-2-amine dihydrochloride

HRID 911787Notes

Reaction equation

HRID 911787 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:10]=[C:11]([S:22]CCC(OC)=O)[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1.Br[CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)[CH3:31]>>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[C:14]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH3:21])[N:20]=2)=[N:13][CH:12]=[C:11]([S:22][CH:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[CH3:31])[CH:10]=1

Participants

3

Reactant 2

HCID 153736572-(1-Bromoethyl)pyridineHCID 24764616Methyl 3-(5-(2-chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate

Product 1

HCID 86631474N-(3-(2-chlorophenylthio)-5-(1-(pyridin-2-yl)ethylthio)pyridin-2-yl)-4-methylthiazol-2-amine dihydrochloride

Procedure

Prepared according to the method of Example 16 from methyl 3-(5-(2-chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate (prepared according to Example 49), and 2-(1-bromoethyl)pyridine. 1H NMR (d6-DMSO) δ 8.54 (d, 1H), 8.19 (bs, 1H), 7.97 (m, 1H), 7.61 (dd, 1H), 7.50 (m, 2H), 7.37 (m, 2H), 7.04 (bs, 2H), 6.52 (s, 1H), 4.56 (q, 1H), 2.18 (s, 3H), 1.59 (d, 3H); Mass spectrum (esi) m/z=471.2 (M+H-2HCl).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3a4d8ea1100549acbda162cf36a56247
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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