Hydrochloric Acid → HCID 68612458, compound

HRID 2095398Notes

Reaction equation

HRID 2095398 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([O:23][CH2:24][C@@H:25]3[CH2:29][CH2:28][CH2:27][NH:26]3)[CH:22]=2)[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:30]>CO>[ClH:30].[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([O:23][CH2:24][C@@H:25]3[CH2:29][CH2:28][CH2:27][NH:26]3)[CH:22]=2)[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59371263HCID 59371263, compound

Product 1

HCID 68612458HCID 68612458, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[3(R)-[3-(benzyloxy)propyl]-1-pyrrolidinyl]-5-[(2(S)-pyrrolidinyl)methoxy]pyridine (210 mg, 0.53 mmol) in methanol (0.4 mL) was added 2 N hydrochloric acid (0.88 mL, 3.3 equiv.) under N2. The mixture was stirred for 4 h at room temperature. After evaporation in vacuo, the residue was diluted with water (12 mL) and lyophilized. The lyophilization process was repeated three times to obtain the hydrochloride (250 mg) as a yellowish solid. 1H NMR (D2O, 300 MHz) δ 7.56 (s, 1H), 7.51 (s, 1H), 7.37-7.27 (m, 5H), 6.92 (s, 1H), 4.48 (s, 2H), 4.47 (dd, 1H , J=6.6, 9.9 Hz), 4.25 (dd, 1H, J=7.5, 10.5 Hz), 4.07-4.03 (m, 1H), 3.54 (t, 2H, J=6.3 Hz), 3.45-3.24 (m, 5H), 2.89 (t, 1H, J=8.4 Hz), 2.03-1.95 (m, 5H), 1.91-1.80 (m, 1H), 1.74-1.51 (m, 3H), 1.48-1.38 (m, 2H). LC-MS (ESI) m/z 396 (M+H+). Anal. Calcd. for C24H33N3O2.2.05HCl.0.6H2O: C, 59.92; H, 7.59; N, 8.73; Cl, 15.11. Found: C, 59.86; H, 8.08; N, 8.63; Cl, 15.57.

Workup

  1. customAfter evaporation in vacuo
  2. additionthe residue was diluted with water (12 mL)

Sources & evidence

ORD record
ord-371cbbe67085478aaf559b78d10fd0fe
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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