Hydrochloric Acid → HCID 22961891, compound

HRID 2305183Notes

Reaction equation

HRID 2305183 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([O:11][CH2:12][C@@H:13]2[CH2:16][CH2:15][NH:14]2)[CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=[CH2:3].Cl.CO>CCOCC>[ClH:10].[CH2:1]([C:4]1[CH:5]=[C:6]([O:11][CH2:12][C@@H:13]2[CH2:16][CH2:15][NH:14]2)[CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 22961890HCID 22961890, compound

Product 1

HCID 22961891HCID 22961891, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-allyl-3-(2-(S)-azetidinylmethoxy)-6-chloropyridine in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: mp 90-92° C., 1H NMR (D2O) δ 2.70 (q, 2H, J=8.5 Hz), 3.52 (d, 2H, J=6.5 Hz), 4.02-4.20 (m, 2H), 4.42 (d, 1H, J=4.0 Hz), 4.93 (m, 1H), 5.08-5.22 (m, 2H), 5.99 (m, 1H), 7.50 (d, 1H, J=3.0 Hz), 8.05 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 239 (M+H)+. Anal. Calcd for C12H15ClN2O.1.4 HCl: C, 49.74; H, 5.70; N, 9.67. Found: C, 49.99; H, 5.78; N, 9.41. [α]25D −6.9 (c 0.6, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-852c9ef42cf04fa6974cbd24a999859a
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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