Hydrazine → HCID 68328171, compound

HRID 634336Notes

Reaction equation

HRID 634336 reaction equation
[CH:1]([NH:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]3[N+:19]([O-])=O)=[N:8][N:9]=1)([CH3:3])[CH3:2].NN>CO.[Ni]>[NH2:19][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([C:7]3[O:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:9][N:8]=3)[CH:11]=2)[NH:15][CH:14]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 68328141HCID 68328141, compound

Product 1

HCID 68328171HCID 68328171, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a suspension of Raney-Ni (100 mg) in MeOH (2 mL) was added N-isopropyl-5-(3-nitro-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (200 mg, 0.698 mmol) followed by addition of NH2NH2 (0.2 mL). The reaction mixture was stirred at RT for 1 h. The mixture was then filtered through a plug of Celite and the filtrate was concentrated. The residue was treated with water and the resulting suspension was filtered, washed with water and dried. The crude product was purified by washing with petroleum ether (2×5 mL) to afford 5-(3-amino-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (50 mg, 27%) as a brown solid. MS (ESI, pos. ion) m/z: 258.2 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 10.43 (s, 1H), 8.02 (s, 1H), 7.46-7.49 (m, 2H), 7.30 (d, 1H, J=8.4 Hz), 6.67 (brs, 1H), 4.27 (s, 2H), 3.70-3.76 (m, 1H), 1.23 (d, 6H, J=6.4 Hz).

Workup

  1. filtrationThe mixture was then filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was treated with water
  4. filtrationthe resulting suspension was filtered
  5. washwashed with water
  6. customdried
  7. customThe crude product was purified
  8. washby washing with petroleum ether (2×5 mL)

Sources & evidence

ORD record
ord-bcbbaa3fcf94407ebe7bf97b2805bbe4
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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