Diisopropylethylamine → 2-[4-([1,3]Thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]nicotinonitrile

HRID 1828305Notes

Reaction equation

HRID 1828305 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[N:25]=[CH:24][CH:23]=[CH:22][C:19]=2[C:20]#[N:21])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>>[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[CH2:16][CH2:17][N:12]([C:18]2[N:25]=[CH:24][CH:23]=[CH:22][C:19]=2[C:20]#[N:21])[CH2:13][CH2:14]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27372032-(Piperazin-1-yl)pyridine-3-carbonitrileHCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 100883802-[4-([1,3]Thiazolo[5,4-b]pyridin-2-ylmethyl)-1-piperazinyl]nicotinonitrile

Procedure

The product from Example 38A (150 mg, 0.81 mmol), 2-(1-piperazinyl)nicotinonitrile (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 2.75 (m, 4H) 3.68 (m, 4H) 4.07 (s, 2H) 6.94 (m, 1H) 7.56 (m, 1H) 8.08 (dd, J=7.80, 2.03 Hz, 1H) 8.33 (dd, J=8.31, 1.53 Hz, 1H) 8.42 (dd, J=4.75, 1.70 Hz, 1H) 8.60 (dd, J=4.58, 1.53 Hz, 1H); (ESI) m/z 337 (M+H)+.

Sources & evidence

ORD record
ord-32c662aa732f4114815a4c0ae616c4ff
Source dataset
uspto-grants-2006_06
Patent number
US07057042B2

Reaction notes

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