Ethyl Acetate → 4-[4-([1,3]Thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]phenol

HRID 2377705Notes

Reaction equation

HRID 2377705 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.[N:12]1([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CC(=O)OCC>>[N:11]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH2:2][N:15]1[CH2:14][CH2:13][N:12]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 92467p-(1-Piperazinyl)phenolHCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 103590224-[4-([1,3]Thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]phenol

Procedure

The product from Example 38A (150 mg, 0.81 mmol), 4-(1-piperazinyl)phenol (160 mg, 0.98 mmol), and D1 EA (280 μL, 1.6 mmol) were processed as described in Example 38B to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.73 (m, 4H) 3.02 (m, 4H) 4.03 (s, 2H) 6.72 (m, 4H) 7.56 (dd, J=8.14, 4.75 Hz, 1H) 8.33 (dd, J=8.14, 1.70 Hz, 1H) 8.59 (dd, J=4.58, 1.53 Hz, 1H): (ESI) m/z 327 (M+H)+.

Sources & evidence

ORD record
ord-e8c740828cb64a11a847fe69c0da655b
Source dataset
uspto-grants-2008_12
Patent number
US07470691B2

Reaction notes

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