HCID 11585745, compound → HCID 11520198, compound

HRID 2378122Notes

Reaction equation

HRID 2378122 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]([N:14]1[C:23]2[C:18](=[N:19][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=2)[C@@H:17]([N:28]([CH2:35][C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=2)[C:29]2[N:30]=[N:31][N:32]([CH3:34])[N:33]=2)[CH2:16][C@H:15]1[CH2:50][CH3:51])=[O:13])C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][CH2:10][O:11][C:12]([N:14]1[C:23]2[C:18](=[N:19][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=2)[C@@H:17]([N:28]([CH2:35][C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:43])[F:44])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=2)[C:29]2[N:30]=[N:31][N:32]([CH3:34])[N:33]=2)[CH2:16][C@H:15]1[CH2:50][CH3:51])=[O:13]

Participants

4

Reactant 1

HCID 11585745HCID 11585745, compound

Product 1

HCID 11520198HCID 11520198, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Stir a mixture of (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid 2-benzyloxy-ethyl ester (69 mg, 94 μmol) and Pd/C 10% (7 mg) in MeOH (1 mL) under a hydrogen atmosphere for 1 h. Filter the mixture over a pad of Celite®. Wash the solids with dichloromethane. Concentrate the filtrate and purified by silica gel chromatography (elution with hexane/ethyl acetate) to afford the title compound (45 mg, 75%). MS (ES+): 642 (M+H).

Workup

  1. filtrationFilter the mixture over a pad of Celite®
  2. washWash the solids with dichloromethane
  3. concentrationConcentrate the filtrate
  4. custompurified by silica gel chromatography (elution with hexane/ethyl acetate)

Sources & evidence

ORD record
ord-25c1c2c946f9425f9cecef46ff8463db
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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