Acetonitrile → HCID 86609634, compound

HRID 1162011Notes

Reaction equation

HRID 1162011 reaction equation
NN.[N+:3]([C:6]1[CH:7]=[C:8]([N:15]2[CH2:20][CH2:19][NH:18][CH:17]3[CH2:21][S:22](=[O:25])(=[O:24])[CH2:23][CH:16]23)[C:9]2O[CH:12]=[CH:11][C:10]=2[CH:14]=1)([O-])=O.CC#N.C1C[O:32]CC1>CCO.[Ni]>[O:25]=[S:22]1(=[O:24])[CH2:21][CH:17]2[CH:16]([N:15]([C:8]3[O:32][C:11]4[CH:12]=[CH:7][C:6]([NH2:3])=[CH:14][C:10]=4[CH:9]=3)[CH2:20][CH2:19][NH:18]2)[CH2:23]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 9321Hydrazine2×HCID 66892777HCID 66892777, compound2×

Product 1

HCID 86609634HCID 86609634, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

Raney-nickel (slurry in ethanol; 2 mL) and hydrazine (204 mL, 4.20 mmol) were added to 1-(5-nitro-1-benzofuran-7-yl)octahydrothieno[3,4-b]pyrazine 6,6-dioxide (0.354 g, 1.05 mmol; Intermediate 35) in a mixture of THF (20 mL) and EtOH (80 mL). The resulting mixture was stirred at room temperature overnight and then more Raney-nickel (slurry in ethanol; 2 mL) and hydrazine (204 mL, 4.20 mmol) were added and stirring was continued overnight. The mixture was filtered through Celite and the solvent was removed in vacuo to afford 0.338 g (quantitative). HPLC 90%, RT: 0.782 (System A; 10-97% MeCN over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 2.79 (dd, J=12.49, 7.30 Hz, 1H) 2.90-3.25 (m, 4H) 3.43-3.64 (m, 3H) 3.91-3.94 (m, 1H) 5.01-5.07 (m, 1H) 6.33 (d, J=1.98 Hz, 1H) 6.61 (dd, J=12.99, 2.10 Hz, 2H) 7.62 (d, J=1.98 Hz, 1H). LC-MS 308 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. filtrationThe mixture was filtered through Celite
  4. customthe solvent was removed in vacuo
  5. customto afford 0.338 g (quantitative)
  6. customHPLC 90%, RT

Sources & evidence

ORD record
ord-38fecd3423424e09b60ef3b1d48f7e04
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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