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

HRID 335085Notes

Reaction equation

HRID 335085 reaction equation
[ClH:1].Cl.CC1N=C([C:9]2[C:14]([S:15][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH3:17])=[CH:13][N:12]=[C:11]([NH2:24])[C:10]=2[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)SC=1.[CH3:32][C:33]1[N:34]=[C:35](NC2N=CC(SCCC(OC)=O)=CC=2OC2C=CC=CC=2)[S:36][CH:37]=1.CC([O-])(C)C.[K+].BrC(C1C=CC=CN=1)C>>[ClH:1].[CH3:32][C:33]1[N:34]=[C:35]([NH:24][C:11]2[C:10]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:9][C:14]([S:15][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH3:17])=[CH:13][N:12]=2)[S:36][CH:37]=1

Participants

5

Reactant 4

HCID 153736572-(1-Bromoethyl)pyridineHCID 23665647Potassium tert-butoxideHCID 24765636Methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoateHCID 866782274-Methylthiazol-2-yl-3-phenoxy-5-(1-(pyridin-2-yl)ethylthio)pyridin-2-amine dihydrochloride

Product 1

HCID 86678226N-(4-methylthiazol-2-yl)-3-phenoxy-5-(1-(pyridin-2-yl)ethylthio)pyridin-2-amine hydrochlorideYield 30.8%

Procedure

Preparation of N-(4-methylthiazol-2-yl-3-phenoxy-5-(1-(pyridin-2-yl)ethylthio)pyridin-2-amine dihydrochloride: Following the procedure in Example 16, methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate (0.325 g, 0.809 mmol), 1M potassium 2-methylpropan-2-olate (2.83 mL, 2.83 mmol), and 2-(1-bromoethyl)pyridine (0.151 g, 0.809 mmol) were reacted to provide N-(4-methylthiazol-2-yl)-3-phenoxy-5-(1-(pyridin-2-yl)ethylthio)pyridin-2-amine hydrochloride (0.114 g, 30.8%) after reverse phase purification and HCl salt formation. 1H NMR (d6-DMSO) δ 8.58 (d, 1H), 8.09 (m, 1H), 8.04 (d, 1H), 7.58 (d, 2H), 7.45 (t, 2H), 7.23 (t, 1H), 7.02 (d, 2H), 6.95 (d, 1H), 6.79 (s, 1H), 4.67 (q, 1H), 2.28 (s, 3H), 1.62 (d, 3H); Mass spectrum (esi) m/z=421.1 (M+H-2HCl).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c15d5b9751c8484c92e63dfcfa70ef4a
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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