Hydrochloric Acid → 1-[3-[5-[(2(S)-Azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(S)-propanol Hydrochloride

HRID 2095347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095347
[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH2:19][C@@H:20]([OH:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=[CH:17][CH:18]=2)[CH:10]=[N:11][CH:12]=1.[ClH:29]>CO>[ClH:29].[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:14]=[C:15]([CH2:19][C@@H:20]([OH:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=[CH:17][CH:18]=2)[CH:10]=[N:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 593713341-[3-[5-[(2(S)-azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(S)-propanol

Produkt 1

HCID 686120371-[3-[5-[(2(S)-Azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(S)-propanol Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-[3-[5-[(2(S)-azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(S)-propanol (130 mg, 0.35 mmol) in methanol (1 mL) was added 2M hydrochloric acid (0.53 mL) at 0° C. under N2. The solution was stirred for 2 h at room temperature and then evaporated. Water (8 mL) was added to dissolve the residue, and the solution was lyophilized. The residue was dissolved in 12 mL of water, and the solution was re-lyophilized to give the hydrochloride (145 mg) as a colorless solid. 1H NMR (D2O, 300 MHz) δ 8.65 (br s, 1H), 8.49 (br s, 1H), 8.35 (br s, 1H), 7.57-7.46 (m, 3H), 7.42 (m, 1H), 7.33-7.22 (m, 5H), 4.96 (m, 1H), 4.57 (d, 2H, J=3.9 Hz), 4.17-4.03 (m, 3H), 2.99-2.62 (m, 6H). LC-MS (ESI) m/z 375 (M+H+). Anal. Calcd. for C24H26N2O2.2.1HCl.1.25H2O: C, 60.87; H, 6.51; N, 5.92; Cl, 15.72. Found: C, 60.87; H, 6.50; N, 5.85; Cl, 15.61.

Aufarbeitung

  1. customevaporated
  2. additionWater (8 mL) was added
  3. dissolutionto dissolve the residue
  4. dissolutionThe residue was dissolved in 12 mL of water

Quellen und Nachweise

ORD-Eintrag
ord-63ebfac4fcec4c69a713313b02b70e97
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445684B2

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