Hydrochloric Acid → HCID 86750808, compound

HRID 2305128Notes

Reaction equation

HRID 2305128 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)[CH:5]=[N:6][C:7]=1[Cl:8].[ClH:23]>O1CCOCC1>[ClH:8].[ClH:23].[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][NH:12]2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22872666HCID 22872666, compound

Product 1

HCID 86750808HCID 86750808, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine from step 69a (150 mg) was stirred with HCl in dioxane (3 mL) at room temperature for 16 hours. The precipitate formed was triturated with Et2O, and the solid was dried under high vacuum to afford the title compound (99.2 mg). mp 230° C. MS (CI/NH3) m/z 291/293 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 1.89-2.02 (m, 1h), 2.05-2.21 (m, 2H), 2.21-2.35 (m, 1H), 3.42 (t, J=7.2 Hz, 2H), 4/12 (m, 1H), 4.25 (dd, J=7.8, 10.5 Hz, 1H), 4.47 (dd, J=3.2, 10.5 Hz, 1H), 7.90 (d, J=2.7 Hz, 1H), 8.13 (d, J=2.7 Hz, 1H). Anal. Calcd for C10H12N2OBrCl.2 HCl: C, 36.61; H, 3.99; N, 8.54. Found: C, 36.69; H, 3.91; N, 8.41. [α]25D=−14.80° (c 0.25, MeOH).

Workup

  1. customThe precipitate formed
  2. customwas triturated with Et2O
  3. customthe solid was dried under high vacuum

Sources & evidence

ORD record
ord-c881b243bcca4eac9e217eb7cd376ef9
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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