Water → HCID 178514427, compound

HRID 1631441Notes

Reaction equation

HRID 1631441 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](OCC)=[O:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][NH2:28].O>C(O)C>[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([NH:27][NH2:28])=[O:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962Water3×HCID 9321Hydrazine2×HCID 178472438HCID 178472438, compound

Product 1

HCID 178514427HCID 178514427, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 13B (750 mg, 2.134 mmol) in ethanol (5 mL) was treated with hydrazine.H2O (1.036 mL, 21.34 mmol), stirred at 80° C. for 2 h. No product was observed so more hydrazine.H2O (1.036 mL, 21.34 mmol) was added, and the solution was stirred at 150° C. in sealed tube overnight. Upon cooling, water was added and the resulting white solid was collected by filtration, washed with water and air dried to provide 14A (754 mg, >quantitative yield) as a white solid. MS (ES): m/z=338.3 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 7.16-7.40 (m, 10H); 6.58 (br. s, 1H); 3.76 (br. s, 2H); 3.55 (s, 4H); 2.42-2.51 (m, 1H); 1.79-1.97 (m, 5H); 1.25-1.42 (m, 4H).

Workup

  1. temperatureUpon cooling
  2. filtrationthe resulting white solid was collected by filtration
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-444df3b372b74eb395df5405ef51ddfb
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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