Hydrochloric Acid → HCID 86755890, compound

HRID 365900Notes

Reaction equation

HRID 365900 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])=[CH:4][C:3]=1[C:16]1[CH:17]=[N:18][CH:19]=[N:20][CH:21]=1.Cl.O.CO>CCOCC>[ClH:1].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])=[CH:4][C:3]=1[C:16]1[CH:21]=[N:20][CH:19]=[N:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 962WaterHCID 54462599HCID 54462599, compound

Product 1

HCID 86755890HCID 86755890, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-chloro-3-(1-methyl-2-(R)-pyrrolidinylmethoxy)-5-(5-pyrimidinyl)pyridine in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: mp 195-197° C.; 1H NMR (D2O) δ 2.02-2.18 (m, 2H), 2.24 (m, 1H), 2.40 (m, 1H), 3.05 (s, 3H), 3.26 (m, 1H), 3.36 (m, 1H), 3.95 (m, 1H), 4.40 (dd, 1H, J=6.0, 11.0 Hz), 4.57 (dd, 1H, J=3.0, 10.0 Hz), 7.66 (d, 1H, J=3.0 Hz), 8.24 (d, 1H, J=3.0 Hz), 8.99 (s, 2H), 9.21 (s, 1H); MS (CI/NH3) m/z 306 (M+H)+. Anal. Calcd for C15H17ClN4O.1.6 HCl.0.1 H2O: C, 49.37; H, 5.19; N, 15.35. Found: C, 49.55; H, 5.13; N, 15.02. [α]25D +8.1 (c 1.2, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-8e5450a17ba149b9b16382fd7202a476
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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