1,2-Dichloroethane → HCID 57788120, compound

HRID 539561Notes

Reaction equation

HRID 539561 reaction equation
[C:1]([C@H](C1C=CC=CC=1)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:18](Cl)CCl.C[C:23]1[CH:28]=[CH:27]N=[C:25]([NH2:29])[C:24]=1[CH3:30].[NH2:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH:38]=[N:37][CH:36]=[CH:35]2.CN([CH:45]=[O:46])C>>[C:4]([O:3][C:1](=[O:2])[NH:29][C@H:25]([C:24]1[CH:23]=[CH:28][CH:27]=[CH:18][CH:30]=1)[C:45]([NH:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH:38]=[N:37][CH:36]=[CH:35]2)=[O:46])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 5889916-AminoisoquinolineHCID 110078842-Amino-3,4-dimethylpyridineHCID 68602053HCID 68602053, compound

Product 1

HCID 57788120HCID 57788120, compound

Procedure

To (R)-2-Boc-2-phenylacetic acid in DMF was added EDC, dimethyl aminopyridine (“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 phenyl-ethylcarbamate (E1).

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-062df20f6b474463b96d20231fc8b89f
Source dataset
uspto-grants-2014_10
Patent number
US08871757B2

Reaction notes

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