1,2-Dichloroethane → HCID 59563773, compound

HRID 1944144Notes

Reaction equation

HRID 1944144 reaction equation
[C:1]([OH:6])(=[O:5])[CH2:2][CH2:3][CH3:4].C(Cl)CCl.O[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:29]([NH:31][C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[CH:38]=[N:37][CH:36]=[CH:35]3)=[O:30])[CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:15][CH:14]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:1]([O:6][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([CH2:20][NH:21][C:22]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:28])[C:29]([NH:31][C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[CH:38]=[N:37][CH:36]=[CH:35]3)=[O:30])=[CH:17][CH:18]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 264Butyric AcidHCID 59563703HCID 59563703, compound

Product 1

HCID 59563773HCID 59563773, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To butyric acid in pyridine was added EDC, DMAP, and tert-butyl 2-(4-(hydroxymethyl)phenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E139), and the solution was 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 (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-5% MeOH/CH2Cl2 gradient) gave pure 4-(3-(tert-butoxycarbonylamino)-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl)benzyl butyrate (E148).

Workup

  1. customthe solution was capped
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. dry with materialThe organics were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5da4ef58e71443169bd797ca6bcd9437
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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