Water → Ethyl 2-(3-(tert-butylamino)propyl)-9-isopropoxy-8-methoxy-1-(thiophen-2-yl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate

HRID 1971655Notes

Reaction equation

HRID 1971655 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]3[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([CH2:23][CH2:24][CH2:25]OS(C)(=O)=O)[C:15]([C:31]4[S:32][CH:33]=[CH:34][CH:35]=4)=[C:12]32)=[CH:7][C:6]=1[O:36][CH3:37])([CH3:3])[CH3:2].[C:38]([NH2:42])([CH3:41])([CH3:40])[CH3:39].O>CN1CCCC1=O>[C:38]([NH:42][CH2:25][CH2:24][CH2:23][C:16]1[C:15]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)=[C:12]2[C:13]3[C:8](=[CH:7][C:6]([O:36][CH3:37])=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:14]=3)[CH2:9][CH2:10][N:11]2[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:41])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 58124861Ethyl 9-isopropoxy-8-methoxy-2-(3-(methylsulfonyloxy)propyl)-1-(thiophen-2-yl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate

Product 1

HCID 66919826Ethyl 2-(3-(tert-butylamino)propyl)-9-isopropoxy-8-methoxy-1-(thiophen-2-yl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 30 mg of 6c and 20 mg of tert-butyl amine in 1 ml of N-methylpyrolidone was heated in a microwave oven at 120° C. for 30 min. The reaction mixture was cooled, poured into 5 ml of water and extracted with ethyl acetate. The product was purified by chromatography over silica gel, using a gradient of CH2Cl2/methanol as eluent, to provide 25 mg of 6d;

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe product was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-ead653142fd04283926fca696dddb57f
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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