Triethylamine → Ethyl 7-azetidin-1-yl-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1696936Notes

Reaction equation

HRID 1696936 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][N:9]2[CH2:12][CH2:13][C:14]#[N:15])=[CH:4][CH:3]=1.Cl.[NH:23]1[CH2:26][CH2:25][CH2:24]1.C(N(CC)CC)C>C(#N)C.O>[N:23]1([C:2]2[N:11]=[C:10]3[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][N:9]3[CH2:12][CH2:13][C:14]#[N:15])=[CH:4][CH:3]=2)[CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 12308726Azetidine hydrochlorideHCID 87333475Ethyl 7-chloro-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 67275510Ethyl 7-azetidin-1-yl-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of EXAMPLE 81B (16 g), azetidine hydrochloride (12.2 g) and triethylamine (21.9 mL) in acetonitrile (500 mL) was stirred for 2 hours, treated with triethylamine (900 mg), stirred for one hour, diluted with water (1.5 L), stirred for 1 hour, and filtered.

Workup

  1. stirringstirred for 1 hour
  2. filtrationfiltered

Sources & evidence

ORD record
ord-7288e3162c064e249db908c8feb139b9
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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