Ether hydrochloride → HCID 52945146, compound

HRID 2095382Notes

Reaction equation

HRID 2095382 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22]2)[CH:20]=1)=O)(C)(C)C.[ClH:30].CCOCC>CO>[ClH:30].[N:21]1([C:19]2[CH:18]=[N:17][CH:16]=[C:15]([O:14][CH2:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)[CH:20]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 49783405HCID 49783405, compound

Product 1

HCID 52945146HCID 52945146, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[[N-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]-5-(1-indolinyl)pyridine (71 mg, 0.18 mmol) in MeOH (0.2 mL) was added 2N anhydrous HCl/ether (1 mL) under Ar at room temperature. The mixture was stirred at room temperature overnight. After the solvent was evaporated, the residue was dissolved in deionized water. The aqueous solution was washed twice with EtOAc, then filtered over a cotton plug. The water was removed under reduced pressure at 35° C. After lyophilization from water, the hydrochloride (71 mg) was obtained as yellow solid. [α]20D+7.0 (c 1.0 g/L, MeOH). 1H NMR (D2O, 400 MHz) δ 7.97 (s, 1H), 7.83 (s, 1H), 7.41 (s, 1H), 7.12 (d, 1H, J=7.2 Hz), 7.05 (m, 2H), 6.82 (t, 1H, J=7.2 Hz), 4.45 (dd, 1H, J=3.2 Hz, J=10.4 Hz), 4.31 (dd, 1H, J=7.6 Hz, J=10.4 Hz), 4.15 (m, 1H), 3.78 (t, 2H, J=8.4 Hz), 3.45 (t, 2H, J=7.2 Hz), 3.01 (t, 2H, J=8.4 Hz), 2.32 (m, 1H), 2.14 (m, 2H), 1.97 (m, 1H). 13C NMR (D2O, 100 MHz) δ 156.2, 142.5, 141.9, 132.2, 126.7, 125.3, 121.9, 121.5, 118.2, 114.2, 109.6, 67.3, 58.1, 51.0, 45.6, 26.6, 25.5, 23.0. HRMS (ESI) calcd for C18H22N3O (M+H+) m/z 296.1763, found 296.1758. Anal. Calcd. for C18H21N3O.3.0HCl.0.1H2O: C, 53.18; H, 6.00; N, 10.34; Cl, 26.16. Found: C, 53.27; H, 6.18; N, 10.26; Cl, 26.03.

Workup

  1. customAfter the solvent was evaporated
  2. dissolutionthe residue was dissolved in deionized water
  3. washThe aqueous solution was washed twice with EtOAc
  4. filtrationfiltered over a cotton plug
  5. customThe water was removed under reduced pressure at 35° C

Sources & evidence

ORD record
ord-8266ab3a833d4542b0854e3558f1ba9d
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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