tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate → N-(3-(2-chlorophenylthio)-5-(piperidin-4-ylmethylthio)pyridin-2-yl)-4-methylthiazol-2-amine dihydrochloride

HRID 911788Notes

Reaction equation

HRID 911788 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][CH2:23][CH2:24][C:25](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.BrCC1C[CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]1>>[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][CH2:23][CH:24]2[CH2:25][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:10]=1

Participants

3

Reactant 2

HCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 24764616Methyl 3-(5-(2-chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate

Product 1

HCID 24764619N-(3-(2-chlorophenylthio)-5-(piperidin-4-ylmethylthio)pyridin-2-yl)-4-methylthiazol-2-amine dihydrochloride

Procedure

Prepared according to the method of Example 16 using methyl 3-(5-(2-chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate and tert-butyl 4-(bromomethyl)piperidine-1-carboxylate. 1H NMR (d6-DMSO) δ 12.15 (bs, 1H), 10.05 (bs, 1H), 8.64 (m, 1H), 8.32 (m, 2H), 7.63 (m, 1H), 7.36 (m, 2H), 6.52 (s, 1H), 3.22 (m, 2H), 2.79 (m, 4H), 2.17 (s, 3H), 1.86 (m, 2H), 1.61 (m, 1H), 1.36 (m, 2H); Mass spectrum (esi) m/z=463.0 (M+H-2HCl).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1df31fd5e1374eaea96444f2727eca10
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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