Carbon Dioxide → 6-[5-Chloro-4-(1-hydroxy-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide

HRID 712704Notes

Reaction equation

HRID 712704 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:11]2[CH:12]=[N:13][C:14]3[NH:15][CH2:16][CH2:17][CH2:18][C:19]=3[CH:20]=2)[C:7]=1[CH:8]([OH:10])[CH3:9].[NH2:21][C:22](N)=[O:23].CO.C(=O)=O>CC(O)C.CCO>[Cl:1][C:2]1[C:7]([CH:8]([OH:10])[CH3:9])=[C:6]([C:11]2[CH:20]=[C:19]3[C:14](=[N:13][CH:12]=2)[N:15]([C:22]([NH2:21])=[O:23])[CH2:16][CH2:17][CH2:18]3)[CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 887MethanolHCID 1176UreaHCID 1176671651-[3-Chloro-5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-4-yl]-ethanol

Product 1

HCID 863053696-[5-Chloro-4-(1-hydroxy-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

Two enantiomers of 1-[3-chloro-5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-4-yl]-ethanol are each converted to Compounds 175 and 176 in Table 1 according to the procedure of Urea Formation Method II (Analytical conditions: LUX 5μ Cellulose 4 Analytical column; 30% 1:1:1 MeOH:EtOH:IPA (1% DEA):CO2 @ 3 mL/min; 40° C.; 200 bars; Retention time, Compound 176: 5.2 min, Compound 175: 6.0 min).

Sources & evidence

ORD record
ord-b8f66f203cdd462596df0449fc61628f
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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