Diisopropylethylamine → 2-{[4-(6-Methyl-2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine

HRID 1768372Notes

Reaction equation

HRID 1768372 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][C:13]1[N:18]=[C:17]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>>[CH3:12][C:13]1[N:18]=[C:17]([N:19]2[CH2:24][CH2:23][N:22]([CH2:2][C:3]3[S:4][C:5]4[C:10]([N:11]=3)=[CH:9][CH:8]=[CH:7][N:6]=4)[CH2:21][CH2:20]2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27369461-(6-Methylpyridin-2-yl)piperazineHCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 99964352-{[4-(6-Methyl-2-pyridinyl)-1-piperazinyl]methyl}[1,3]thiazolo[5,4-b]pyridine

Procedure

The product from Example 38A (150 mg, 0.81 mmol), 1-(6-methyl-2-pyridinyl)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 1H NMR (300 MHz, DMSO-d6) δ 2.68 (m, 4H) 3.32 (s, 3H) 3.53 (m, 4H) 4.04 (s, 2H) 6.54 (m, 1H) 6.61 (d, J=8.48 Hz, 1H) 7.40 (m, 1H) 7.56 (dd, J=8.31, 4.58 Hz, 1H) 8.33 (dd, J=8.31, 1.53 Hz, 1H); (ESI) m/z 326 (M+H)+.

Sources & evidence

ORD record
ord-aec54867c755499398599f3f394f09a9
Source dataset
uspto-grants-2007_06
Patent number
US07235661B2

Reaction notes

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