Hydrochloric Acid → HCID 9949184, compound

HRID 1780343Notes

Reaction equation

HRID 1780343 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([O:14][CH2:15][C@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3C(OC(C)(C)C)=O)[CH:10]=[N:11][C:12]=2[Cl:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>O1CCOCC1>[ClH:13].[C:1]1([C:7]2[CH:8]=[C:9]([O:14][CH2:15][C@H:16]3[CH2:20][CH2:19][CH2:18][NH:17]3)[CH:10]=[N:11][C:12]=2[Cl:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22872686HCID 22872686, compound

Product 1

HCID 9949184HCID 9949184, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the 5-phenyl-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine compound from Example 69b (164 mg) was added HCl in dioxane (3 mL). The mixture was stirred at room temperature for 40 hours. The solvent was removed under vacuum at 50° C., and the residue was triturated with ether. The solid was dried under high vacuum to afford the title compound. mp 178°-180° C. MS (DCI/NH3) m/z 289 (M+H)+. 1 H NMR (D2O, 300 MHz) δ: 1.27-2.10 (m, 1H), 2.03-2.18 (m, 2H), 2.22-2.31 (m, 1H), 3.41 (t, J=7.5 Hz, 2H), 4.13 (m, 1H), 4.26 (m, 1H), 4.46 (dd, J=3.4, 10.8 Hz, 1H), 7.54 (m, 6H), 8.12 (d, J=3.0 Hz, 1H). Anal. Calcd for C16H17N2OCl·1.2 HCl: C, 57.79; H, 5.52; N, 8.42. Found: C, 57.73; H, 6.5.58; N, 8.27. [α]25D =-10.94° (c 0.64, MeOH).

Workup

  1. customThe solvent was removed under vacuum at 50° C.
  2. customthe residue was triturated with ether
  3. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-41059db007114b3891909319be4679cb
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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