Hydrazine → HCID 66673247, compound

HRID 423694Notes

Reaction equation

HRID 423694 reaction equation
[NH2:1][NH2:2].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29]C4C=CC([N+]([O-])=O)=CC=4)=O)[CH2:23][CH2:22]3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5]>C(O)C>[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([C:27]([NH:1][NH2:2])=[O:29])[CH2:23][CH2:22]3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:6]

Participants

4

Reactant 2

HCID 9321Hydrazine2×HCID 66673010HCID 66673010, compound

Product 1

HCID 66673247HCID 66673247, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Hydrazine (0.140 mL, 4.45 mmol) was added to a mixture of 4-nitrophenyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (456 mg, 0.89 mmol) in ethanol (30 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The mixture was charged with additional ethanol (30 mL) and hydrazine (5 mL, 159 mmol), stirred at reflux until homogeneous (15 min), then at ambient temperature overnight. The mixture was concentrated to dryness, charged with 4:1 EtOH:CH2Cl2 and MP-Carbonate (8 g). The mixture was stirred at ambient temperature for 2 h, filtered, washed with 4:1 EtOH:CH2Cl2, and the filtrate was concentrated to give 352 mg (98%) of 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbohydrazide as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.43 (d, 1H, J=2.9 Hz), 8.28 (d, 2H, J=8.6 Hz), 8.06 (d, 1H, J=8.9 Hz), 7.99 (d, 2H, J=8.6 Hz), 7.61 (bs, 1H), 7.54 (dd, 1H, Ja=8.8 Hz, Jb=3.0 Hz), 4.03-3.92 (m, 4H), 3.84 (d, 2H, J=3.2 Hz), 3.25 (s, 3H), 2.74-2.64 (m, 2H), 2.05-1.88 (m, 1H), 1.79-1.67 (m, 2H), 1.23-1.09 (m, 2H); LRMS (ESI), m/z 405 (M+H).

Workup

  1. stirringstirred
  2. temperatureat reflux until homogeneous (15 min)
  3. customat ambient temperature
  4. customovernight
  5. concentrationThe mixture was concentrated to dryness
  6. additioncharged with 4:1 EtOH
  7. stirringThe mixture was stirred at ambient temperature for 2 h
  8. filtrationfiltered
  9. washwashed with 4:1 EtOH
  10. concentrationCH2Cl2, and the filtrate was concentrated

Sources & evidence

ORD record
ord-9d48a91a0b024f58af835eee90f03019
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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