6-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)(methyl)amino]-2-chloro-5-fluoronicotinonitrile → 2-Chloro-5-fluoro-6-[(3-hydroxypropyl)(methyl)amino]nicotinonitrile

HRID 603473Notes

Reaction equation

HRID 603473 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH3:23])[C:13]1[C:20]([F:21])=[CH:19][C:16]([C:17]#[N:18])=[C:15]([Cl:22])[N:14]=1)(C(C)(C)C)(C)C>C(O)C.Cl.O>[Cl:22][C:15]1[N:14]=[C:13]([N:12]([CH2:11][CH2:10][CH2:9][OH:8])[CH3:23])[C:20]([F:21])=[CH:19][C:16]=1[C:17]#[N:18]

Participants

3

Reactant 1

HCID 866045996-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)(methyl)amino]-2-chloro-5-fluoronicotinonitrile

Product 1

HCID 866046002-Chloro-5-fluoro-6-[(3-hydroxypropyl)(methyl)amino]nicotinonitrileYield 100.6%

Reagents, catalysts & solvents 1

HCID 86604601Ethanol water hydrochloric acidSolvent

Procedure

A mixture of 6-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(methyl)amino]-2-chloro-5-fluoronicotinonitrile (Example 310, 0.73 g, 2.04 mmol) in ethanol/HCl/water (95:1:4) (50 mL) was stirred at rt for 18 h, and then concentrated under reduced pressure. The residue was passed through a plug of silica gel with ethyl acetate as the eluent to give the product (0.5 g, 100%) as a waxy yellow solid. 1H NMR (400 MHz, CD3OD) δ 7.54 (d, 1H), 3.65 (dt, 2H), 3.54 (t, 2H), 3.18 (d, 3H), 1.85-1.77 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f8fe92a043b4a2c965b61f56de8435f
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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