Stannous chloride dihydrate → HCID 66739216, compound

HRID 1641026Notes

Reaction equation

HRID 1641026 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[C:6]([C:16](=[O:28])[C:17]([NH:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:18])=[CH:5]1)([CH3:3])[CH3:2].O.O.[Cl:31][Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[ClH:31].[NH2:13][C:10]1[CH:11]=[C:12]2[C:7]([C:6]([C:16](=[O:28])[C:17]([NH:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)=[O:18])=[CH:5][N:4]2[CH:1]([CH3:3])[CH3:2])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 46221740HCID 46221740, compound

Product 1

HCID 66739216HCID 66739216, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the following procedure: 2-(1-isopropyl-6-nitro-1H-indol-3-yl)-2-oxo-N-(2-(piperidin-1-yl)ethyl)acetamide (500 mg, 1.29 mmol) was dissolved in EtOAc. SnCl2.2H2O (1.39 g, 6.50 mmol) was added portionwise and the mixture was heated at reflux for 8 hr. The reaction mixture was then cooled and treated with sat. NaHCO3. After stirring at RT for 30 min., the reaction mixture was extracted with EtOAc, dried over MgSO4, concentrated down and then converted to the HCl salt to yield the title compound (350 mg, 76% yield): 1H NMR (400 MHz, DMSO-d6): δ 10.30 (NH2 and NH+, br, s, 3H), 9.04 (s, 1H), 8.87 (s, 1H), 8.26 (s, 1H), 7.67 (s, 1H), 7.25 (s, 1H), 4.77 (m, 1H), 3.60 (m, 2H), 3.17 (m, 2H), 2.86 (m, 2H), 1.74 (m, 4H), 1.50 (d, 6H), 1.28 (m, 2H), 1.04 (m, 2H); MS (ESI) m/z: Calculated for C20H28N4O2: 356.2. Found: 357.2 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 8 hr
  4. temperatureThe reaction mixture was then cooled
  5. extractionthe reaction mixture was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated down

Sources & evidence

ORD record
ord-27abf9914545432fa1706a69dacbcd96
Source dataset
uspto-grants-2012_02
Patent number
US08114894B2

Reaction notes

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