Hydrochloric Acid → HCID 68611421, compound

HRID 2095404Notes

Reaction equation

HRID 2095404 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 59371584HCID 59371584, compound

Product 1

HCID 68611421HCID 68611421, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[3(S)-[3-(benzyloxy)propyl]-1-pyrrolidinyl]-5-[(2(S)-pyrrolidinyl)methoxy]pyridine (150 mg, 0.38 mmol) in methanol (0.3 mL) was added 2 N hydrochloric acid (0.63 mL, 3.3 equiv.) under N2. The reaction 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 (170 mg, 88%) as a yellowish solid. 1H NMR (D2O, 300 MHz) δ 7.56 (s, 1H), 7.50 (s, 1H), 7.34-7.30 (m, 5H), 6.92 (s, 1H), 4.47 (s, 2H), 4.44 (dd, 1H, J=10.5, 3.3 Hz), 4.24 (dd, 1H, J=10.5, 7.5 Hz), 4.06-4.03 (m, 1H), 3.53 (t, 2H, J=6.3 Hz), 3.44-3.23 (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 C24H33N3O2.2.3HCl.1.65H2O: C, 56.62; H, 7.64; N, 8.25; Cl, 16.02. Found: C, 56.53; H, 7.93; N, 8.51; Cl, 16.31.

Workup

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

Sources & evidence

ORD record
ord-c10872d421b34f2fbacda2daa9ddc675
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

Loading…