HCID 86610589, compound → HCID 16725629, compound

HRID 506358Notes

Reaction equation

HRID 506358 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[N:24]=[C:23]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[C:22]([CH:40]=[CH:41][C:42]([OH:44])=[O:43])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:45][CH3:46])=[O:5])[CH3:2]>O1CCCC1.CO.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[N:24]=[C:23]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[C:28]([C:36]([F:39])([F:37])[F:38])[CH:27]=3)[C:22]([CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:45][CH3:46])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 86610589HCID 86610589, compound

Product 1

HCID 16725629HCID 16725629, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2R,4S)-4-{[3,5-Bis(trifluoromethyl)benzyl]-[5-(2-carboxyvinyl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (500 mg) is dissolved in a mixed solution of tetrahydrofuran (15 ml) and methanol (5 ml), then thereto is added 10% palladium/carbon (160 mg), and the mixture is stirred at room temperature under hydrogen for 3 hours and 30 minutes. The reaction solution is filtered, and concentrated under reduced pressure to give (2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(2-carboxyethyl)-pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (498 mg). MS (m/z): 656 [M+H]+

Workup

  1. filtrationThe reaction solution is filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e10c33ad41c8458684746d741f4ab34f
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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