1,2-Dichloroethane → HCID 57788110, compound

HRID 539566Notes

Reaction equation

HRID 539566 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:19])[C@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([O-:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[NH2:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[CH:31]=[N:30][CH:29]=[CH:28]2>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH:31]1[C:32]2[C:27](=[CH:26][C:25]([NH:24][C:10](=[O:12])[C@H:9]([N:8]([CH3:19])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:34][CH:33]=2)[CH:28]=[CH:29][N:30]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 5889916-AminoisoquinolineHCID 86310788HCID 86310788, compound

Product 1

HCID 57788110HCID 57788110, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To (R)-2-(tert-butoxycarbonyl(methyl)amino)-2-phenylacetate (E6) in DMF was added EDC, DMAP and 6-aminoisoquinoline. This mixture was stirred for 4 hours and the reaction was washed with NaHCO3 (sat), extracted with EtOAc, dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, Hexanes/EtOAc) gave pure (R)-tert-butyl 2-(isoquinolin-6-ylamino)-2-oxo-1-phenylethyl(methyl)carbamate (E7).

Workup

  1. washthe reaction was washed with NaHCO3 (sat)
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7554303ef00a450190b86d2c36df646f
Source dataset
uspto-grants-2014_10
Patent number
US08871757B2

Reaction notes

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