Hydrochloric Acid → HCID 86639678, compound

HRID 1426130Notes

Reaction equation

HRID 1426130 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:22][CH2:23][CH2:24]C(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+].[Cl:35][CH2:36][C:37]1C=C[CH:40]=[C:39]([O:43][CH3:44])[CH:38]=1.Cl>>[ClH:35].[CH3:44][O:43][C:39]1[CH:40]=[C:24]([CH:36]=[CH:37][CH:38]=1)[CH2:23][S:22][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH3:21])[N:20]=2)=[N:13][CH:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 699943-Methoxybenzyl chlorideHCID 16660505Methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86639678HCID 86639678, compoundYield 75.4%

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-(chloromethyl)-3-methoxybenzene (0.024 mL, 0.17 mmol) were reacted according to the method of Example 43 to afford 5-(3-methoxybenzylthio)-3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (61.7 mg, 75.4% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 7.84 (d, 1H), 7.57 (m, 3H), 7.44-7.33 (m, 3H), 7.17 (t, 3H), 6.80 (m, 4H), 5.29 (s, 2H), 4.17 (s, 2H), 3.68 (s, 3H), 2.30 (s, 3H); Mass spectrum (apci) m/z=450.0 (100), 359.0 (80), 238.0 (75).

Sources & evidence

ORD record
ord-23182c7ed6a64bd2809704f74e758a27
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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