Hydrochloric Acid → (S)-1-(3-chloro-6-(6-(5-ethylpyridin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amine

HRID 57831노트

반응식

HRID 57831 반응식
[Cl:1][C:2]1[C:3]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31]C(=O)OC(C)(C)C)[CH2:26]2)=[N:4][C:5]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[C:21]([CH2:23][CH3:24])[CH:22]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1.Cl>CO.O1CCOCC1>[Cl:1][C:2]1[C:3]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH2:31])[CH2:26]2)=[N:4][C:5]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[C:21]([CH2:23][CH3:24])[CH:22]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 86707036tert-butyl N-[(3S)-1-[3-chloro-6-[6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate

생성물 1

HCID 86707037(S)-1-(3-chloro-6-(6-(5-ethylpyridin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amine수율 36.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of tert-butyl N-[(3S)-1-[3-chloro-6-[6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (0.0446 mmol; 23.8 mg) in Methanol (10 mL) was added hydrochloric acid, 4.0 M in 1,4-Dioxane (5 mL). The resulting mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 117 (7.0 mg, 33%). 1H NMR (400 MHz, DMSO) δ 9.36-9.31 (s, 1H), 9.18-9.11 (m, 2H), 8.74-8.65 (s, 1H), 8.58-8.52 (d, J=1.9 Hz, 1H), 8.34-8.30 (s, 1H), 8.02-7.97 (d, J=8.4 Hz, 1H), 7.60-7.55 (d, J=8.4 Hz, 1H), 3.95-3.81 (dd, J=27.5, 10.2 Hz, 2H), 3.06-2.97 (t, J=10.2 Hz, 1H), 2.93-2.84 (t, J=9.5 Hz, 1H), 2.81-2.72 (m, 3H), 1.98-1.90 (d, J=12.6 Hz, 1H), 1.89-1.80 (d, J=13.3 Hz, 1H), 1.79-1.68 (d, J=12.9 Hz, 1H), 1.68-1.48 (s, 2H), 1.31-1.26 (t, J=7.6 Hz, 3H), 1.26-1.20 (m, 1H); MS (ESI) m/z: 434.2 [M+H]+

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-0aeeb7424afc4353b1f43c875563f77c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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