2-{6-[3-(Tert-butyl-dimethyl-silanyloxy)-propoxy]-pyridin-3-yl}-4,5,6,7-tetrahydro-benzothiazole → 3-[5-(4,5,6,7-Tetrahydro-benzothiazol-2-yl)-pyridin-2-yloxy]-propan-1-ol

HRID 734437Notes

Reaction equation

HRID 734437 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[S:18][C:19]3[CH2:25][CH2:24][CH2:23][CH2:22][C:20]=3[N:21]=2)=[CH:13][CH:12]=1)(C)(C)C>C(O)C.Cl.O>[S:18]1[C:19]2[CH2:25][CH2:24][CH2:23][CH2:22][C:20]=2[N:21]=[C:17]1[C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][OH:6])=[N:16][CH:15]=1

Participants

3

Reactant 1

HCID 578453912-{6-[3-(Tert-butyl-dimethyl-silanyloxy)-propoxy]-pyridin-3-yl}-4,5,6,7-tetrahydro-benzothiazole

Product 1

HCID 578453663-[5-(4,5,6,7-Tetrahydro-benzothiazol-2-yl)-pyridin-2-yloxy]-propan-1-olYield 47.5%

Reagents, catalysts & solvents 1

HCID 86604601Ethanol water hydrochloric acidSolvent

Procedure

A mixture of 2-{6-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-pyridin-3-yl}-4,5,6,7-tetrahydro-benzothiazole (Example 77, 0.29 g, 0.71 mmol) in ethanol/HCl/water (95:1:4; 10 mL) was stirred at rt for 18 h, and then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (1:4 MeOH/CH2Cl2) to give the title compound (0.098 g, 46%). 1H NMR (400 MHz, CDCl3) δ 8.60 (dd, 1H), 8.10 (dd, 1H), 6.75 (dd, 1H), 4.51 (t, 2H), 3.73 (t, 2H), 2.95-3.10 (broad s, 1H), 2.80-2.86 (m, 4H), 2.00-2.12 (m, 2H), 1.80-1.96 (m, 4H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel flash chromatography (1:4 MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-85b6f93f1712429e838ee34ae2a3f779
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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