Hydrochloric Acid → HCID 68612343, compound

HRID 2095305Notes

Reaction equation

HRID 2095305 reaction equation
[ClH:1].C(OC([N:9]1[CH2:12][CH2:11][C@H:10]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C@@H:21]2[CH2:23][C@H:22]2[CH2:24][CH2:25][F:26])[CH:20]=1)=O)(C)(C)C>CCOCC.CO>[ClH:1].[NH:9]1[CH2:12][CH2:11][C@H:10]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C@@H:21]2[CH2:23][C@H:22]2[CH2:24][CH2:25][F:26])[CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68611501HCID 68611501, compound

Product 1

HCID 68612343HCID 68612343, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2M HCl (anhydrous) in ether (2.0 mL) was added to a stirred solution of 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-[(1R,2S)-2-(2-fluoroethyl)cyclopropyl]pyridine (160 mg, 0.45 mmol) in dry MeOH (2.0 mL) at 0° C. The mixture was stirred at room temperature for 12 h. The above solution was concentrated and purified by HPLC to obtain the title compound (97 mg). 1H NMR (CD3OD, 400 MHz) δ 8.40 (br s, 1H), 8.29 (br s, 1H), 7.75 (s, 1H), 4.91-4.85 (m, 1H), 4.63-4.47 (m, 4H), 4.17-4.04 (m, 2H), 2.79-2.58 (m, 2H), 2.04-1.97 (m, 1H), 1.91-1.77 (m, 2H), 1.46-1.34 (m, 1H), 1.26-1.19 (m, 1H), 1.16-1.09 (m, 1H). MS (ESI) m/z 273 (M+Na+).

Workup

  1. concentrationThe above solution was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-8933fadcaf3342d19f910ab64559be05
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

Loading…