Hydrochloric Acid → HCID 86639680, compound

HRID 1426132Notes

Reaction equation

HRID 1426132 reaction equation
[CH2:1]([O: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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].BrCC1C[CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]1.[ClH:50]>>[ClH:50].[ClH:50].[CH2:1]([O: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][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 16660505Methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86639680HCID 86639680, compoundYield 64.6%

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 tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (46.9 mg, 0.17 mmol) were reacted according to the method of Example 43 to afford 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(piperidin-4-ylmethylthio)pyridin-2-amine dihydrochloride (54.4 mg, 64.6% yield) as a white solid after HCl salt formation. 1H NMR (d6-DMSO) δ 9.20 (bs, 1H), 9.00 (bs, 1H), 7.97 (m, 1H), 7.65 (m, 3H), 7.45-7.30 (m, 3H), 6.90 (s, 1H), 5.41 (s, 2H), 3.75-3.45 (m, 3H), 3.20 (m, 2H), 2.95 (m, 2H), 2.76 (m, 2H), 2.34 (s, 3H), 1.88 (m, 2H), 1.64 (m, 1H), 1.42 (m, 2H); Mass spectrum (apci) m/z=427.1 (M+H-2HCl).

Sources & evidence

ORD record
ord-3fabda31f0404c289179d781dd822a47
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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