1,2-Dichloroethane → HCID 59563712, compound

HRID 1944183Notes

Reaction equation

HRID 1944183 reaction equation
[C:1]1([CH:7]([CH2:11][O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.[NH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH:34]=[N:33][CH:32]=[CH:31]2>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH:34]1[C:35]2[C:30](=[CH:29][C:28]([NH:27][C:8](=[O:9])[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:11][O:12][Si:13]([CH:17]([CH3:19])[CH3:18])([CH:20]([CH3:22])[CH3:21])[CH:14]([CH3:15])[CH3:16])=[CH:37][CH:36]=2)[CH:31]=[CH:32][N:33]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 5889916-AminoisoquinolineHCID 59563735HCID 59563735, compound

Product 1

HCID 59563712HCID 59563712, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 2-phenyl-3-(triisopropylsilyloxy)propanoic acid (E400) in pyridine was added EDC, DMAP, and 6-aminoisoquinoline, and the solution was flushed with N2, capped, and stirred overnight. The mixture was poured into NaHCO3(sat) and extracted with EtOAC. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (3-4% MeOH/CH2Cl2) gave pure N-(isoquinolin-6-yl)-2-phenyl-3-(triisopropylsilyloxy)propanamide (E401).

Workup

  1. customthe solution was flushed with N2
  2. customcapped
  3. additionThe mixture was poured into NaHCO3(sat)
  4. extractionextracted with EtOAC
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-23817914ebac4d36946e71b4ce490449
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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