1-(2-Methoxyphenyl)piperazine → 2-{[4-(2-Methoxyphenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine

HRID 1828311Notes

Reaction equation

HRID 1828311 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][O: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][O: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 13461-(2-Methoxyphenyl)piperazineHCID 81531DiisopropylethylamineHCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 104050022-{[4-(2-Methoxyphenyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine

Procedure

The product from Example 38A (200 mg, 1.1 mmol), 1-(2-methoxyphenyl)piperazine (229 mg, 1.2 mmol), and DIEA (380 μL, 2.2 mmol) were processed as described in Example 38B to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.74 (m, 4H) 3.02 (m, 4H) 3.78 (s, 3H) 4.04 (s, 2H) 6.91 (m, 3H) 7.56 (dd, J=8.31, 4.75 Hz, 2H) 8.33 (dd, J=8.14, 1.70 Hz, 1H) 8.59 (dd, J=4.75, 1.70 Hz, 1H); (ESI) m/z 341 (M+H)+.

Sources & evidence

ORD record
ord-d0ff49941df0449f95843dc97a9b2d08
Source dataset
uspto-grants-2006_06
Patent number
US07057042B2

Reaction notes

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