Diisopropylethylamine → {4-[2-(Methylthio)phenyl]-1-piperazinyl}methyl[1,3]thiazolo[5,4-b]pyridine

HRID 1768375Notes

Reaction equation

HRID 1768375 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.[CH3:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C>>[CH3:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][N:23]([CH2:2][C:3]2[S:4][C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[CH:7][N:6]=3)[CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27368951-(2-(Methylthio)phenyl)piperazineHCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 10066878{4-[2-(Methylthio)phenyl]-1-piperazinyl}methyl[1,3]thiazolo[5,4-b]pyridine

Procedure

The product from Example 38A (150 mg, 0.81 mmol), 1-[2-(methylthio)phenyl]piperazine (160 mg, 0.98 mmol), and DIEA (280 μL, 1.6 mmol) were processed as described in Example 38B to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.37 (s, 3H) 2.75 (m, 4H) 2.97 (m, 4H) 4.06 (s, 2H) 7.13 (m, 3H) 7.56 (dd, J=8.31, 4.58 Hz, 2H) 8.33 (dd, J=8.14, 1.36 Hz, 1H) 8.59 (dd, J=4.58, 1.53 Hz, 1H); (ESI) m/z 357 (M+H)+.

Sources & evidence

ORD record
ord-3e34fe0428214896b4cc85e8b1d8446f
Source dataset
uspto-grants-2007_06
Patent number
US07235661B2

Reaction notes

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