1,2-Dichloroethane → HCID 59563743, compound

HRID 1944139Notes

Reaction equation

HRID 1944139 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:19]([NH:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[CH:28]=[N:27][CH:26]=[CH:25]3)=[O:20])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:5][CH:4]=1.C(Cl)CCl.[CH:36]1([C:42](O)=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH:36]1([C:42]([O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([CH:9]([CH2:10][NH:11][C:12]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:18])[C:19]([NH:21][C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[CH:28]=[N:27][CH:26]=[CH:25]4)=[O:20])=[CH:7][CH:8]=2)=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 7413Cyclohexanecarboxylic acidHCID 59563703HCID 59563703, compound

Product 1

HCID 59563743HCID 59563743, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To tert-butyl 2-(4-(hydroxymethyl)phenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E139) in pyridine was added EDC, DMAP, and cyclohexanecarboxylic 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 (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 5% MeOH/CH2Cl2) gave pure 4-(3-(tert-butoxycarbonylamino)-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl)benzyl cyclohexanecarboxylate (E142).

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 (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-21f3eca16f994ace97b1306b26b509b8
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

Loading…