Hydrochloric Acid → HCID 86610653, compound

HRID 506392Notes

Reaction equation

HRID 506392 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]([S:40](CCC(OC)=O)(=[O:42])=[O:41])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:49][CH3:50])=[O:5])[CH3:2].[OH-].[Na+].Cl.C(OCC)(=[O:56])C>C(O)C>[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:27]=[C:28]([C:36]([F:37])([F:39])[F:38])[CH:29]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:31]=3)[C:22]([S:40]([OH:41])(=[O:42])=[O:56])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:49][CH3:50])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86610654HCID 86610654, compound

Product 1

HCID 86610653HCID 86610653, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

(2R*,4S*)-4-{[3,5-Bis(trifluoromethyl)benzyl]-[5-(2-methoxycarbonyl-ethanesulfonyl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (141 mg) and 2N aqueous NaOH solution (384 μl) are dissolved in ethanol (3 ml), and the mixture is stirred at 50° C. for 30 minutes. To the reaction solution is added 2N aqueous HCl solution (385 μl), and stirred overnight. To the reaction mixture is added ethyl acetate, and the organic layer is washed with saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; chloroform:methanol=9:1→4:1) to give (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-(5-sulfopyrimidin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (64 mg). MS (m/z): 662 [M−H]−.

Workup

  1. stirringstirred overnight
  2. washthe organic layer is washed with 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; chloroform:methanol=9:1→4:1)

Sources & evidence

ORD record
ord-d098d47f9dff4eb3858440f4d6fa534a
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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