Hydrochloric Acid → HCID 22961858, compound

HRID 365892Notes

Reaction equation

HRID 365892 reaction equation
[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([Cl:19])=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)[CH:12]=1.[ClH:20].O.CO>CCOCC>[ClH:19].[ClH:20].[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([Cl:19])=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 962WaterHCID 22961857HCID 22961857, compound

Product 1

HCID 22961858HCID 22961858, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-(2-(S)-azetidinylmethoxy)-6-chloro-5-(5-pyrimidinyl)pyridine from step c above in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: mp 144° C. (dec.); 1H NMR (D2O) δ 2.70 (q, 2H, J=8.5 Hz), 4.04-4.18 (m, 2H), 4.48 (d, 2H, J=4.0 Hz), 4.97 (m, 1H), 7.70 (d, 1H, J=3.0 Hz), 8.28 (d, 1H, J=3.0 Hz), 9.00 (s, 2H), 9.22 (s, 1H); MS (CI/NH3) m/z 278 (M+H)+. Anal. Calcd for C13H13ClN4O.1.5 HCl.0.1 H2O: C, 46.86; H, 4.45; N, 16.81. Found: C, 47.11; H, 4.63; N, 16.42. [α]25D -9.20 (c 0.25, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-649bc182bd454d3a8af5a46f89a3e0ee
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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