Acetic Acid → HCID 178487870, compound

HRID 1422975Notes

Reaction equation

HRID 1422975 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14](=[O:39])[NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([CH:37]=O)=[CH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[N:32]=3)[N:27]=[CH:26][C:25]=2[Cl:36])[CH2:18][CH2:17]1)([CH3:12])([CH3:11])[CH3:10].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.C(OCC)(=O)C>[C:9]([O:13][C:14](=[O:39])[NH:15][C@H:16]1[CH2:17][CH2:18][C@H:19]([C:22]([CH2:37][NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[N:32]=3)[N:27]=[CH:26][C:25]=2[Cl:36])[CH2:20][CH2:21]1)([CH3:12])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 178487871HCID 178487871, compound

Product 1

HCID 178487870HCID 178487870, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzylamine (360 mg, 3.36 mmol, 3.0 eq) is added at room temperature to a stirred solution of {trans-4-[2-(3-chloro-6-methoxy-[1,5]naphthyridin-4-yl)-1-formyl-vinyl]-cyclohexyl}-carbamic acid tert-butyl ester (500 mg, 1.12 mmol, 1.0 eq) in ethanol (20 mL), followed by acetic acid (337 mg, 5.61 mmol, 5.0 eq) and sodium cyanoborohydride (352 mg, 5.61 mmol, 5.0 eq). After 2 hours stirring at room temperature, the reaction mixture is extracted with ethyl acetate (3×20 mL) and a saturated sodium hydrogen carbonate aqueous solution (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 3:1 to 1:1, v/v) to afford {trans-4-[1-(benzylamino-methyl)-2-(3-chloro-6-methoxy-[1,5]naphthyridin-4-yl)-vinyl]-cyclohexyl}-carbamic acid tert-butyl ester as a light yellow solid (320 mg, 53% yield).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue that
  6. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-47c2fe0678c04c3babdc401c329e2fe7
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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