1,2-Dichloroethane → HCID 59563732, compound

HRID 1944129Notes

Reaction equation

HRID 1944129 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)=[O:19])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.C(Cl)CCl.[CH3:35][C:36]1([C:39](O)=[O:40])[CH2:38][CH2:37]1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:35][C:36]1([C:39]([O:1][C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH2:9][NH:10][C:11]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:17])[C:18]([NH:20][C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[CH:27]=[N:26][CH:25]=[CH:24]4)=[O:19])=[CH:4][CH:3]=2)=[O:40])[CH2:38][CH2:37]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 813261-Methylcyclopropanecarboxylic acidHCID 59563693HCID 59563693, compound

Product 1

HCID 59563732HCID 59563732, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To tert-butyl 2-(4-hydroxyphenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E8) in pyridine was added EDC, DMAP, and 1-methylcyclopropanecarboxylic acid, and the solution was flushed with N2, capped, and stirred overnight. The mixture was poured into EtOAc/NaHCO3(sat) and the aqueous layer was further extracted with EtOAc. The organics were dried (Na2SO4), filtered, and evaporated. Column chromatography 5% MeOH/CH2Cl2 gave pure 4-(3-(tert-butoxycarbonylamino)-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl)phenyl 1-methylcyclopropanecarboxylate (E11).

Workup

  1. customthe solution was flushed with N2
  2. customcapped
  3. additionThe mixture was poured into EtOAc/NaHCO3(sat)
  4. extractionthe aqueous layer was further extracted with EtOAc
  5. dry with materialThe organics were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cee78a307a784b4f90c63d2cbef965e2
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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