Hydrazine → HCID 22220325, compound

HRID 1061289Notes

Reaction equation

HRID 1061289 reaction equation
O1C2(CC[N:8]([C:11](=[O:31])[CH2:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:30][CH2:29][C:24]5([O:28][CH2:27][CH2:26][O:25]5)[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=O)CC2)OCC1.[NH2:32]N>C(O)C.O1CCCC1>[O:28]1[C:24]2([CH2:29][CH2:30][N:21]([C:18]3[CH:17]=[CH:16][C:15]([C:13]4[NH:32][NH:8][C:11](=[O:31])[CH:12]=4)=[CH:20][CH:19]=3)[CH2:22][CH2:23]2)[O:25][CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 22220588HCID 22220588, compound

Product 1

HCID 22220325HCID 22220325, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-3-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-phenyl]-propane-1,3-dione (which was obtained in Example 143) (0.43 g, 1 mmol) was dissolved in a mixture of ethanol (10 mL) and tetrahydrofuran (4 mL). The solution was treated with 0.08 mL (2.4 mmol) of hydrazine and heated at reflux for 4 days. After cooling to room temperature, the resulting suspension was filtered, and the precipitate was washed with ethanol and dried in vacuo to give 0.24 g of light yellow solid; 1H NMR (DMSO-d6) δ 1.67-1.71 (t, 4H), 3.29-3.32 (t, 4H), 3.91 (s, 4H), 5.72 (s, 1H), 6.97 (d, 2H), 7.48 (d, 2H), 9.50 (brs, 1H), 11.80 (brs, 1H); MS (ES) m/z: 302 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 days
  3. filtrationthe resulting suspension was filtered
  4. washthe precipitate was washed with ethanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e047bc0c34464248a2f54e2ea7b60cd6
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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