1,4-Dioxane → 5-[1-(6-Piperazin-1-yl-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]thiazole

HRID 57818Notes

Reaction equation

HRID 57818 reaction equation
[S:1]1[C:5]([C:6]2[N:11]=[CH:10][C:9]3[CH:12]=[N:13][N:14]([C:15]4[N:20]=[C:19]([N:21]5[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]5)[CH:18]=[CH:17][CH:16]=4)[C:8]=3[CH:7]=2)=[CH:4][N:3]=[CH:2]1.O1CCOCC1>Cl>[N:21]1([C:19]2[N:20]=[C:15]([N:14]3[C:8]4[CH:7]=[C:6]([C:5]5[S:1][CH:2]=[N:3][CH:4]=5)[N:11]=[CH:10][C:9]=4[CH:12]=[N:13]3)[CH:16]=[CH:17][CH:18]=2)[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 312751,4-Dioxane2×HCID 86707025HCID 86707025, compound

Product 1

HCID 727150485-[1-(6-Piperazin-1-yl-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]thiazoleYield 72%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of tert-butyl 4-[6-(6-thiazol-5-ylpyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate in hydrogen chloride (4 mol/l) in dioxane (1.5 mL, 6.0 mmol) and dioxane 1.0 mL was stirred at RT 14 h. The reaction was concentrated. The crude product was submitted for reverse phase HPLC to give 109 (44 mg) in 72% yield. MS (ESI) m/z: 364.1. 1H NMR (400 MHz, DMSO) δ 9.20 (d, J=8.2 Hz, 2H), 8.94 (s, 1H), 8.64-8.59 (m, 1H), 8.43 (s, 1H), 7.77 (t, J=8.1 Hz, 1H), 7.23 (d, J=7.7 Hz, 1H), 6.81 (d, J=8.4 Hz, 1H), 3.65-3.57 (m, 4H), 2.96-2.88 (m, 4H)

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-9620e75b047f45a59228b986dc829d27
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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