HCID 86610568, compound → HCID 86610567, compound

HRID 506341Notes

Reaction equation

HRID 506341 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][CH:19]([C:34]2[N:39]=[CH:38][C:37]([NH:40][C:41](=[O:54])[CH2:42][NH:43]C(OCC3C=CC=CC=3)=O)=[CH:36][N:35]=2)[C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=2)[CH2:8][C@H:7]1[CH2:55][CH3:56])=[O:5])[CH3:2]>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][CH:19]([C:34]2[N:35]=[CH:36][C:37]([NH:40][C:41](=[O:54])[CH2:42][NH2:43])=[CH:38][N:39]=2)[C:20]2[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[C:22]([C:30]([F:31])([F:32])[F:33])[CH:21]=2)[CH2:8][C@H:7]1[CH2:55][CH3:56])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 86610568HCID 86610568, compound

Product 1

HCID 86610567HCID 86610567, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2R*,4S*)-4-({5-[2-(Benzyloxycarbonylamino)acetylamino]pyrimidin-2-yl}-[3,5-bis(trifluoromethyl)benzyl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (631 mg) is dissolved in methanol (10 ml), 10% palladium/carbon (100 mg) is added thereto and then the mixture is stirred at room temperature under hydrogen for 30 minutes. The reaction solution is filtered, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; chloroform:methanol=1:0→9:1) to give (2R*,4S*)-4-{[5-(2-aminoacetylamino)pyrimidin-2-yl]-[3,5-bis(trifluoromethyl)benzyl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (463 mg). MS (m/z): 626 [M+H]+

Workup

  1. filtrationThe reaction solution is filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue is purified by column chromatography (silica gel; chloroform:methanol=1:0→9:1)

Sources & evidence

ORD record
ord-d29cb8c429d64c22a217a6c4c11383c0
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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