Hydrochloric Acid → 3-(2-(4-Methylthiazol-2-ylamino)pyridin-4-ylthio)phenol

HRID 910964Notes

Reaction equation

HRID 910964 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]3[S:24][CH:25]=[C:26]([CH3:28])[N:27]=3)[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.C1COCC1.Cl>O>[CH3:28][C:26]1[N:27]=[C:23]([NH:22][C:18]2[CH:17]=[C:16]([S:15][C:11]3[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=3)[CH:21]=[CH:20][N:19]=2)[S:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 248258774-(3-(tert-butyldimethylsilyloxy)phenylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine

Product 1

HCID 578989303-(2-(4-Methylthiazol-2-ylamino)pyridin-4-ylthio)phenolYield 89.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3 dram vial was charged with 4-(3-(tert-butyldimethylsilyloxy)phenylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.470 g, 1.09 mmol and THF (2 mL) and 6M HCl (1 mL) were added. The reaction mixture was stirred at room temperature overnight, then diluted with water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give desired product (0.309 g, 89.6% yield) as yellow solid. 1H NMR (DMSO) δ 11.07 (s, 1H), 9.84 (s, 1H), 8.08 (d, 1H), 7.32 (t, 1H), 6.98 (m, 1H), 6.92 (m, 2H), 6.76 (d, 1H), 6.59 (dd, 1H), 6.51 (d, 1H), 2.20 (d, 3H); Mass spectrum (esi) m/z=316 (100) (M+H).

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bfea7175e848432188fb7f59cba0e04c
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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