Tin dichloride dihydrate → HCID 89628486, compound

HRID 1747738Notes

Reaction equation

HRID 1747738 reaction equation
[CH2:1]([C:5]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[CH2:10][N:11]([C:14](=[O:26])/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)[CH2:12][CH2:13][C:8]=2[C:7](=[O:27])[O:6]1)[CH:2]([CH3:4])[CH3:3].O.[Sn](Cl)Cl>CO>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1/[CH:16]=[CH:15]/[C:14]([N:11]1[CH2:12][CH2:13][C:8]2[C:7](=[O:27])[O:6][C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:9]=2[CH2:10]1)=[O:26]

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 71610394HCID 71610394, compound

Product 1

HCID 89628486HCID 89628486, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-3-isobutyl-5-(3-(2-nitrophenyl)acryloyl)-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (25 mg, 0.092 mmol) and tin(II)chloride hydrate (83 mg, 0.369 mmol) was heated in methanol (15 mL) for 2 hours. The reaction mixture was cooled to room temperature, concentrated to dryness, and re-dissolved in ethyl acetate (20 mL). The organic solution was washed with sat. NaHCO3 solution (5 mL), brine (5 mL), dried (MgSO4), and concentrated. Purification by column chromatography (4 g, SiO2, 0 to 5% chloroform/methanol/ammonium hydroxide 80:18:2 in dichloromethane) provided (E)-5-(3-(2-aminophenyl)acryloyl)-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one as a white solid: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.83-1.01 (m, 6H), 1.62-1.75 (m, 1H), 1.84 (dd, J=14.69, 7.16 Hz, 1H), 2.35 (dd, J=14.69, 4.52 Hz, 1H), 2.43-2.55 (m, 2H), 3.51 (m, J=5.70 Hz, 1H), 3.82-4.00 (m, 3H), 4.09 (d, J=19.59 Hz, 1H), 4.84 (d, J=19.21 Hz, 1H), 6.66-6.86 (m, 3H), 7.18 (t, J=7.54 Hz, 1H), 7.29-7.48 (m, 6H), 7.83 (d, J=15.07 Hz, 1H); MS m/z 417 (M+H)+, 439 (M+23)+, 415 (M−H)−.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionre-dissolved in ethyl acetate (20 mL)
  3. washThe organic solution was washed with sat. NaHCO3 solution (5 mL), brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by column chromatography (4 g, SiO2, 0 to 5% chloroform/methanol/ammonium hydroxide 80:18:2 in dichloromethane)

Sources & evidence

ORD record
ord-858057ef216d45148b359189a3630ece
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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