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

HRID 57818노트

반응식

HRID 57818 반응식
[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

참가 물질

4

반응물 2

HCID 312751,4-Dioxane2회HCID 86707025HCID 86707025, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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)

후처리

  1. concentrationThe reaction was concentrated

출처 및 근거

ORD 기록
ord-9620e75b047f45a59228b986dc829d27
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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