Stannous chloride dihydrate → [2-Amino-4-(benzyloxy)-5-methoxyphenyl][4-(4-quinazolinyl)piperazino]methanone

HRID 1876824Notes

Reaction equation

HRID 1876824 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[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[CH:27][N:26]=3)[CH2:21][CH2:20]2)=[O:18])=[C:11]([N+:35]([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>[NH2:35][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[CH2:24][CH2:23][N:22]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=[CH:27][N:26]=2)[CH2:21][CH2:20]1)=[O:18]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 66882459[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanone

Product 1

HCID 24936159[2-Amino-4-(benzyloxy)-5-methoxyphenyl][4-(4-quinazolinyl)piperazino]methanoneYield 119.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanone (600 mg, 1.2 mmol) was dissolved in methanol (10 mL), SnCl2.2H2O (810 mg, 3.6 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 (450 mg, 95% yield). This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product (8d) (672 mg, 80% yield). 1H NMR (CDCl3) δ 3.20-3.30 (m, 4H), 3.65-3.75 (m, 4H), 3.95 (s, 3H), 5.20 (s, 2H), 6.20 (s, broad NH2), 6.45-6.55, (t, 1H) 6.70 (s, 1H), 7.30-7.50 (m, 5H), 7.55-7.65 (t, 1H), 7.65 (s, 1H), 7.70-7.90, (m, 2H), 7.85-7.95, (m, 2H); FABMS: 470 (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 (450 mg, 95% yield)
  8. customThis was further purified by column chromatography

Sources & evidence

ORD record
ord-4d18c5f72d6a49058147e059b7b2f772
Source dataset
uspto-grants-2012_11
Patent number
US08309726B2

Reaction notes

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