1,2-Dichloroethane → 1253955-17-7

HRID 1944142Notes

Reaction equation

HRID 1944142 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(Cl)CCl.O[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:34]([NH:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[CH:43]=[N:42][CH:41]=[CH:40]3)=[O:35])[CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:20][CH:19]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH:24]([CH2:25][NH:26][C:27]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:33])[C:34]([NH:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[CH:43]=[N:42][CH:41]=[CH:40]3)=[O:35])=[CH:22][CH:23]=1)=[O:5]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 118972,4-Dimethylbenzoic acidHCID 59563703HCID 59563703, compound

Product 1

HCID 595638051253955-17-7

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 2,4-dimethylbenzoic 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 2,4-dimethylbenzoate (E145).

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-b83666e042044551afc8aecd29e86feb
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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