Hydrochloric Acid → HCID 59404400, compound

HRID 1873675Notes

Reaction equation

HRID 1873675 reaction equation
CO[C:3](=[O:18])[C:4]([C:6]1[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH2:9][N:8]3[CH:7]=1)=O.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][C:29]([NH2:31])=[S:30])=[CH:20]1.C(O[K])(C)(C)C.Cl>C1COCC1.CCOC(C)=O.O>[C:6]1([C:4]2[C:3](=[O:18])[NH:31][C:29](=[S:30])[C:28]=2[C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][CH:20]=2)[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH2:9][N:8]3[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 790201HCID 790201, compoundHCID 59298805methyl 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxoacetateHCID 178418922HCID 178418922, compound

Product 1

HCID 59404400HCID 59404400, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-oxo-acetic acid methyl ester (3.4 g, 14 mmol) and 2-(1H-indol-3-yl)-thioacetamide (2.9 g, 15 mmol) in anhydrous THF (34 mL) at −30° C. under N2 was added dropwise 1M tBuOK in THF (42 mL, 42 mmol). The reaction mixture was allowed warm to room temperature over 2 h. The reaction mixture was cooled to 0° C. and concentrated HCl (42 mL) added slowly. The mixture was allowed warm to room temperature with stirring over 1 h before being diluted with EtOAc and water. The organics were separated, washed with brine and evaporated to yield a dark residue. The residue was purified by column chromatography (SiO2, EtOAc/hexanes). 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-5-thioxo-1,5-dihydro-pyrrol-2-one was obtained as a dark foam (4.7 g, 87%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureThe mixture was allowed warm to room temperature
  3. customThe organics were separated
  4. washwashed with brine
  5. customevaporated
  6. customto yield a dark residue
  7. customThe residue was purified by column chromatography (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-827ea92151524dea86b17f2f6807300a
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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