Sodium Acetate Trihydrate → HCID 66856643, compound

HRID 2400764Notes

Reaction equation

HRID 2400764 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]([CH3:26])[N:19]=[C:20]([CH3:25])[C:21]=3[N+:22]([O-])=O)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.O.[Sn](Cl)Cl.O.O.O.C([O-])(=O)C.[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]([CH3:26])[N:19]=[C:20]([CH3:25])[C:21]=3[NH2:22])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 23665404Sodium Acetate TrihydrateHCID 43835034Tin dichloride dihydrateHCID 66854723HCID 66854723, compound

Product 1

HCID 66856643HCID 66856643, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product obtained in Step B (800 mg) in tetrahydrofuran (8 ml) and methanol (8 ml) at room temperature under nitrogen was added tin(II) chloride monohydrate (2.9 g) and sodium acetate trihydrate (3.5 g). The resulting mixture was stirred at room temperature for 34 hours. The reaction mixture was partitioned between 1M sodium hydroxide and ethyl acetate, stirred for 10 min, the organic layer was separated, dried over sodium sulfate and concentrated. 1-[(E)-3-(4-Chlorophenyl)-allyl]-4-(2,5-dimethyl-4-amino-2H-pyrazol-3-yl)-piperazine (510 mg) was obtained as a red solid. 1H NMR (400 MHz, CDCl3) 2.3 (s, 3H), 2.8 (m, 4H), 3.3 (m, 4H), 3.4 (d, J=9 Hz, 2H), 3.8 (s, 3H), 6.4 (dt, J=18, 9 Hz, 1H), 6.7 (d, J=18 Hz, 1H), 7.3-7.4 (m, 4H); MS (ES+) 151/153 (cinnamyl), 196(M-cinnamyl), 346/348 (M+H+).

Workup

  1. customThe reaction mixture was partitioned between 1M sodium hydroxide and ethyl acetate
  2. stirringstirred for 10 min
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-efe7d7ad3458460bbc95d2acc6aa8839
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

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