Hydrochloric Acid → 5-(2-(1H-imidazol-1-yl)ethylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine dihydrochloride

HRID 1426133Notes

Reaction equation

HRID 1426133 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:22][CH2:23]CC(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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[ClH:35].[Cl:36]C[CH2:38][N:39]1[CH:43]=[CH:42][N:41]=[CH:40]1.Cl>>[ClH:36].[ClH:35].[N:39]1([CH2:38][CH2:23][S:22][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:14]([NH:15][C:16]3[S:17][CH:18]=[C:19]([CH3:21])[N:20]=3)=[N:13][CH:12]=2)[CH:43]=[CH:42][N:41]=[CH:40]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 27575031-(2-chloroethyl)-1H-imidazole hydrochlorideHCID 16660505Methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 727028735-(2-(1H-imidazol-1-yl)ethylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine dihydrochlorideYield 33.6%

Procedure

Methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate (prepared according to Example 42; 70 mg, 0.17 mmol), KOtBu (0.59 mL, 0.59 mmol) and 1-(2-chloroethyl)-1H-imidazole hydrochloride (28.1 mg, 0.17 mmol) were reacted according to the method of Example 43 to afford 5-(2-(1H-imidazol-1-yl)ethylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine dihydrochloride (28.1 mg, 33.6% yield) as a tan solid after HCl salt formation. 1H NMR (d6-DMSO) δ 9.16 (t, 1H), 7.96 (d, 1H), 7.75 (t, 1H), 7.66 (t, 1H), 7.64-7.59 (m, 3H), 7.45-7.33 (m, 3H), 6.77 (s, 1H), 5.34 (s, 2H), 4.35 (t, 2H), 3.47 (t, 2H), 2.29 (d, 3H); Mass spectrum (apci) m/z=424.0 (100) 328.0 (75) 238.0 (35).

Sources & evidence

ORD record
ord-ed94b2ebedfc4209829e06cd24f14ea7
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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