Hydrochloric Acid → HCID 86758468, compound

HRID 2305127Notes

Reaction equation

HRID 2305127 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9](OC[C@H]3CCCN3C(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.[O:29]1[CH2:34][CH2:33]OCC1>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([O:29][CH2:34][C@H:33]3[CH2:8][CH2:9][CH2:10][NH:11]3)=[N:11][C:12]=2[Cl:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 22872686HCID 22872686, compound

Product 1

HCID 86758468HCID 86758468, compound

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 tirred at room temperature for 40 hours. The solvent was removed under vacuum at 50° C., and the residue was triturated with Et2O. The solid was dried under high vacuum to afford the title compound. mp 178-180° C. MS (CI/NH3) m/z 289 (M+H)+. 1H 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 Et2O
  3. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-7915a7cb0d144bdaa90d748c297d4711
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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