Stannous chloride dihydrate → HCID 10111880, compound

HRID 456704Notes

Reaction equation

HRID 456704 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[N:21]=3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:17][C:13]1[CH:12]=[C:11]([C:9]2[N:10]=[C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]3[C:8]=2[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[N:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 10274600HCID 10274600, compound

Product 1

HCID 10111880HCID 10111880, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-{4-[8-chloro-2-(3-nitrophenyl)imidazo[1,2-α]pyridin-3-yl]-2-pyrimidinyl}-N-cyclopentylamine (744 mg, 1.71 mmol) in ethanol (25 mL) was added tin(II) chloride dihydrate (1.62 g, 8.57 mmol). The mixture was heated at 80° C. for 4 hours. The solution was cooled to room temperature and quenched by the dropwise addition of saturated aqueous sodium bicarbonate. Dichloromethane was added and the organic layer was washed with brine. The aqueous layer was extracted with dichloromethane and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (1:1 to 1:2 hexanes:ethyl acetate) provided 4-[2-(3-aminophenyl)-8-chloroimidazo[1,2-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (690 mg, 99%) as a foam. 1H NMR (CDCl3): δ 9.54 (broad, 1H), 8.10 (d, 1H), 7.39 (d, 1H), 7.16 (t, 1H), 7.05 (m, 1H), 6.97 (d, 1H), 6.84 (t, 1H), 6.72 (m, 1H), 6.51 (d, 1H), 5.18 (d, 1H), 4.33 (m, 1H), 3.72 (broad, 2H), 2.14–2.06 (m, 2H), 1.82–1.54 (m, 6H); MS m/z 405 (M+1).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customquenched by the dropwise addition of saturated aqueous sodium bicarbonate
  3. additionDichloromethane was added
  4. washthe organic layer was washed with brine
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined organics were dried over magnesium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-319c1f0aa55c41ffb5be5b99130191db
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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