Ethyl Acetate → HCID 178487808, compound

HRID 1422976Notes

Reaction equation

HRID 1422976 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8](=[O:40])[NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([CH2:31][NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[N:26]=3)[N:21]=[CH:20][C:19]=2Cl)[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].C(OCC)(=O)C>O.O1CCCC1>[C:3]([O:7][C:8](=[O:40])[NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH2:31][N:32]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:19]3[CH:20]=[N:21][C:22]4[C:27]([C:18]=3[CH:17]=2)=[N:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178487870HCID 178487870, compound

Product 1

HCID 178487808HCID 178487808, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of sodium hydroxide (500 mg, 12.5 mmol, 33.6 eq) in water (6 mL) is added at room temperature to a stirred solution of {trans-4-[1-(benzylamino-methyl)-2-(3-chloro-6-methoxy-[1,5]naphthyridin-4-yl)-vinyl]-cyclohexyl}-carbamic acid tert-butyl ester (200 mg, 0.37 mmol, 1.0 eq) in tetrahydrofuran (6 mL). After 16 hours stirring at 60° C., tetrahydrofuran is removed and the residue is extracted with ethyl acetate (3×10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give the crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1 to 3:1, v/v) to afford [trans-4-(1-benzyl-6-methoxy-1,2-dihydro-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-carbamic acid tert-butyl ester as a light yellow solid (110 mg, 59% yield).

Workup

  1. customtetrahydrofuran is removed
  2. extractionthe residue is extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-ffb7244dd1554ba9b005a943f8897aa1
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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