Hydrochloric Acid → HCID 68611916, compound

HRID 2095298Notes

Reaction equation

HRID 2095298 reaction equation
[ClH:1].CCOCC.C(OC([N:14]1[CH2:17][CH2:16][C@H:15]1[CH2:18][O:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([C@H:26]2[CH2:28][C@@H:27]2[CH2:29][CH2:30][F:31])[CH:25]=1)=O)(C)(C)C>CO>[ClH:1].[NH:14]1[CH2:17][CH2:16][C@H:15]1[CH2:18][O:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([C@H:26]2[CH2:28][C@@H:27]2[CH2:29][CH2:30][F:31])[CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68611774HCID 68611774, compound

Product 1

HCID 68611916HCID 68611916, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2M HCl (anhydrous)/ether (2.0 mL) was added to a stirred solution of 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-[(1S,2R)-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 give the title compound (97 mg). 1H NMR (CD3OD, 400 MHz) δ 8.38 (s, 1H), 8.28 (s, 1H), 7.71 (s, 1H), 4.92-4.86 (m, 1H), 4.61-4.48 (m, 4H), 4.18-4.04 (m, 2H), 2.75-2.61 (m, 2H), 2.03-1.97 (m, 1H), 1.91-1.77 (m, 2H), 1.46-1.35 (m, 1H), 1.25-1.19 (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-d1016b97e6db4d0d8ad67474323a0dbf
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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