Hydrochloric Acid → HCID 59441882, compound

HRID 1014322Notes

Reaction equation

HRID 1014322 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:25][CH3:26])=[C:19]([N+:22]([O-])=O)[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:6][CH2:5]1)[CH3:3].O.O.[Sn](Cl)Cl.Cl>C(O)C.CC(N(C)C)=O>[CH3:3][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:25][CH3:26])=[C:19]([NH2:22])[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:6][CH2:5]1)[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 59441921HCID 59441921, compound

Product 1

HCID 59441882HCID 59441882, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 1-{[4-(1-methylethyl)-1-piperazinyl]acetyl}-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (0.60 g, 1.66 mmol) in absolute ethanol (100 mL) and DMA (20 mL) was added tin(II)chloride dihydrate (2.24 g, 9.93 mmols) and 1M HCl(1.0 mL). After overnight stirring, reaction was quenched with excess saturated NaHCO3 solution, stirred for one hr, and filtered through celite which was rinsed with methanol. After organic solvent removal, the aqueous layer was extracted with dichloromethane (2×200 mL), organic layers combined, adsorbed to silica gel and purified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH) to afford 1-{[4-(1-methylethyl)-1-piperazinyl]acetyl}-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine. ESIMS (M+H)+=333.

Workup

  1. customreaction
  2. customwas quenched with excess saturated NaHCO3 solution
  3. stirringstirred for one hr
  4. filtrationfiltered through celite which
  5. washwas rinsed with methanol
  6. customAfter organic solvent removal
  7. extractionthe aqueous layer was extracted with dichloromethane (2×200 mL), organic layers
  8. custompurified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH)

Sources & evidence

ORD record
ord-1e7d4967f0d04c08a9421dcf8a3c645c
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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