Hydrochloric Acid → HCID 86750808, compound

HRID 1780345Notes

Reaction equation

HRID 1780345 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 ether, and the solid was dried under high vacuum to afford the title compound (99.2 mg). mp 230° C. MS (CDI/NH3) m/z 291/293 (M+H)+. 1 H 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 ether
  3. customthe solid was dried under high vacuum

Sources & evidence

ORD record
ord-4c9d282246274d83a6000e020f8af454
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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