Methanol → HCID 67980649, compound

HRID 2407020Notes

Reaction equation

HRID 2407020 reaction equation
[CH3:1][CH:2]([CH3:36])[CH2:3][CH:4]([NH:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:27])=[CH:24][N:23]=1)[C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1.CO.[CH2:39](NCC)C>C(=O)=O>[CH3:1][CH:2]([CH3:36])[CH2:3][CH:4]([NH:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH3:39])=[O:32])=[O:27])=[CH:24][N:23]=1)[C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8021DiethylamineHCID 57389361HCID 57389361, compound

Product 1

HCID 67980649HCID 67980649, compound

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

(+/−)-methyl 3-(6-(3-methyl-1-(6-(4-(trifluoromethyl)phenyl)pyridin-3-yl)butylamino)nicotinamido)propanoate (prepared as described in Example 1.29) was resolved via SFC (Column: Chiralcel OJ-H 250×4.6 mm×5 μm, Mobile phase: 5 to 40% methanol in CO2, modifier: 0.05% diethylamine, flow rate: 2.5 mL/min) to give methyl 3-(6-(3-methyl-1-(6-(4-(trifluoromethyl)phenyl)pyridin-3-yl)butylamino)nicotinamido)propanoate, Isomer 1 (retention time: 7.36 min) and methyl 3-(6-(3-methyl-1-(6-(4-(trifluoromethyl)phenyl)pyridin-3-yl)butylamino) nicotinamido)propanoate, Isomer 2 (retention time: 8.85 min).

Sources & evidence

ORD record
ord-67613e25965f45859675ce22fb44c0f4
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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