Hydrochloric Acid → HCID 22176325, compound

HRID 1797649Notes

Reaction equation

HRID 1797649 reaction equation
C([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([C:24]([NH2:26])=[S:25])=[CH:14][CH:13]=2)(C)(C)C.Cl.C(N(CC)CC)C.[CH:41]1[C:53]2[CH:52]([CH2:54]OC(Cl)=O)[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]=2[CH:44]=[CH:43][CH:42]=1>C(OCC)(=O)C.O>[NH2:26][C:24]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:27])[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:9]([CH2:8][NH:7][C:6](=[O:32])[O:5][CH2:54][CH:52]1[C:53]3[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=3[C:46]3[C:51]1=[CH:50][CH:49]=[CH:48][CH:47]=3)=[C:18]2[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[S:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 343679-Fluorenylmethyl chloroformateHCID 86592074HCID 86592074, compound

Product 1

HCID 22176325HCID 22176325, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl[6-(aminothiocarbonyl)-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (Example 189 (1)) (1.38 g, 3 mmol) was dissolved in a solution of 4N hydrogen chloride in ethyl acetate (10 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure and the residue was suspended in tetrahydrofuran (20 ml). To the obtained mixture were added triethylamine (0.84 ml, 6 mmol) and 9-fluorenylmethylchloroformate (1.16 g, 4.5 mmol) and the mixture was stirred at 0° C. for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 9H-fluoren-9-ylmethyl [6-(aminocarbothioyl)-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (1.52 g, 86.9%) as an amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringthe mixture was stirred at 0° C. for 1 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6009de470d284745aba4c504fd15e74a
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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