Stannous chloride dihydrate → HCID 25014685, compound

HRID 1876822Notes

Reaction equation

HRID 1876822 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[N:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:21][CH2:20]2)=[O:18])=[C:11]([N+:31]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl>CO>[NH2:31][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([O:15][CH3:16])=[CH:13][C:12]=1[C:17]([N:19]1[CH2:20][CH2:21][N:22]([C:25]2[N:26]=[CH:27][CH:28]=[CH:29][N:30]=2)[CH2:23][CH2:24]1)=[O:18]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 66881813HCID 66881813, compound

Product 1

HCID 25014685HCID 25014685, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(2-pyrimidinyl)piperazino-]methanone (7c) (500 mg, 1.11 mmol) was dissolved in methanol (10 mL), SnCl2.2H2O (751 mg, 3.3 mmol) was added and refluxed until the TLC indicated the completion of the reaction. The methanol was evaporated by vacuum and the aqueous layer was then adjusted to pH 8 with 10% NaHCO3 solution and extracted with ethyl acetate (2×30 mL). The combined organic phase was dried over Na2SO4 and evaporated under vacuum to afford the crude This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product (8c) (420 mg, 90% yield). 1H NMR (CDCl3) δ 3.10-3.25 (m, 4H), 3.60-3.80 (m, 4H), 3.95 (s, 3H), 5.20 (s, 2H), 6.20 (s, br), 6.45-6.55 (t, 1H) 6.75 (s, 1H), 7.30-7.55 (m, 5H), 7.80 (s, 1H); FABMS: 419 (M+H)+.

Workup

  1. temperaturerefluxed until the TLC
  2. customthe completion of the reaction
  3. customThe methanol was evaporated by vacuum
  4. extractionextracted with ethyl acetate (2×30 mL)
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. customevaporated under vacuum
  7. customto afford the crude This was
  8. customfurther purified by column chromatography

Sources & evidence

ORD record
ord-61f711cf67b24e8d9a37af5abbe9e18e
Source dataset
uspto-grants-2012_11
Patent number
US08309726B2

Reaction notes

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