Hydrochloric Acid → HCID 16725575, compound

HRID 506349Notes

Reaction equation

HRID 506349 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]([O:40][CH2:41][CH:42]3[CH2:46][O:45]C(C)(C)[O:43]3)=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:49][CH3:50])=[O:5])[CH3:2].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[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:38])([F:37])[F:39])[CH:27]=3)[C:22]([O:40][CH2:41][CH:42]([OH:43])[CH2:46][OH:45])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:49][CH3:50])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86610579HCID 86610579, compound

Product 1

HCID 16725575HCID 16725575, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2R,4S)-4-([3,5-bis(trifluoromethyl)benzyl]-{5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]pyrimidin-2-yl})amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (147 mg) is dissolved in tetrahydrofuran (2 ml), then thereto is added 1N-hydrochloric acid (2 ml), and the mixture is stirred overnight. A saturated aqueous sodium hydrogen carbonate solution is added to the reaction solution and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=3:2→3:7) to give (2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(2,3-dihydroxypropoxy)-pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (72 mg). MS (m/z): 674 [M+H]+

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=3:2→3:7)

Sources & evidence

ORD record
ord-e8170b0e6d704a0c82940ee5daa30fee
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

Loading…