Hydrochloric Acid → N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-2-ylmethylthio)pyridin-2-amine dihydrochloride

HRID 335082Notes

Reaction equation

HRID 335082 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:13]=[CH:12][C:11]([S:14][CH2:15][CH2:16][C:17](OC)=O)=[CH:10][C:9]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:5][CH:6]=1.CC([O-])(C)C.[K+].Br.BrC[C:37]1[CH:42]=[CH:41]C=C[N:38]=1.[Cl-:43].[NH4+].Cl>C1COCC1>[ClH:43].[ClH:43].[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:9]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:10][C:11]([S:14][CH2:15][C:16]3[CH:17]=[CH:41][CH:42]=[CH:37][N:38]=3)=[CH:12][N:13]=2)[S:5][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 23665647Potassium tert-butoxideHCID 24765636Methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate

Product 1

HCID 24765641N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-2-ylmethylthio)pyridin-2-amine dihydrochlorideYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 20 mL vial was charged with methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate (135.8 mg, 0.338 mmol) and THF (0.5 mL). 1M KOtBu in THF (1.184 mL, 1.184 mmol) was added and the reaction mixture was stirred at room temperature for 30 seconds. 2-(Bromomethyl)pyridine hydrobromide (85.55 mg, 0.3382 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. Saturated aqueous ammonium chloride was added and the reaction mixture was extracted with EtOAc. The concentrated residue was purified on silica gel to afford N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-2-ylmethylthio)pyridin-2-amine dihydrochloride (98.2 mg, 60.5% yield) as a pale yellow solid after HCl salt formation. 1H NMR (d6-DMSO) δ 8.66 (dd, 1H), 8.22 (td, 1H), 8.12 (d, 1H), 7.70 (t, 1H), 7.62 (d, 1H), 7.45 (m, 2H), 7.23 (t, 1H), 7.16 (d, 1H), 7.06 (m, 2H), 6.82 (m, 1H), 4.42 (s, 2H), 2.29 (s, 3H); Mass spectrum (esi) m/z=407.2 (100) (M+H-2HCl).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. extractionthe reaction mixture was extracted with EtOAc
  3. customThe concentrated residue was purified on silica gel

Sources & evidence

ORD record
ord-1320a1cca9d84f5696b43437f39584d1
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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