1,2-Dichloroethane → Tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propyl(methyl)carbamate

HRID 1944152Notes

Reaction equation

HRID 1944152 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:32])[CH2:9][CH:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[CH:16][CH:15]=1)[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[NH2:37][C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[CH:44]=[N:43][CH:42]=[CH:41]2>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH:44]1[C:45]2[C:40](=[CH:39][C:38]([NH:37][C:11](=[O:13])[CH:10]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][O:21][Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:29]([CH3:30])[CH3:31])=[CH:18][CH:19]=3)[CH2:9][N:8]([CH3:32])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[CH:47][CH:46]=2)[CH:41]=[CH:42][N:43]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 5889916-AminoisoquinolineHCID 595637453-(Tert-butoxycarbonyl(methyl)amino)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoic acid

Product 1

HCID 59563752Tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propyl(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 3-(tert-butoxycarbonyl(methyl)amino)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoic acid (E204) in pyridine was added was added EDC, DMAP, and 6-aminoisoquinoline, and the solution was stirred overnight at room temperature. The mixture was poured into NaHCO3(sat) and extracted with EtOAc. The organics were dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-6% MeOH/CH2Cl2 gradient) gave pure tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propyl(methyl)carbamate (E205).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-b7fb8d91d6e545d0aa005cc536c4bee3
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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