Water → HCID 178494504, compound

HRID 1631439Notes

Reaction equation

HRID 1631439 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](=O)[C:16]#[C:17][CH2:18][O:19][CH3:20])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][NH2:30].O>CCO>[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:16]=[C:17]([CH2:18][O:19][CH3:20])[NH:30][N:29]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 178495081HCID 178495081, compound

Product 1

HCID 178494504HCID 178494504, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A stirred solution of 13E (150 mg, 0.399 mmol) in EtOH (2 mL) was treated with hydrazine (0.116 mL, 2.397 mmol), and stirred overnight at 75° C. Upon cooling, water was added, the mixture was stirred for 1 h, the resulting white solid was collected by filtration and air dried to yield 13F (125 mg, 80% yield). MS (ES): m/z=390.3 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 7.31 (d, 4H, J=7.0 Hz); 7.18-7.25 (m, 4H); 7.14 (t, 2H, J=7.3 Hz); 5.92 (s, 11H); 4.35 (s, 2H); 3.58 (s, 4H); 3.30 (s, 3H); 2.44-2.55 (m, 2H); 1.89-2.01 (m, 4H); 1.23-1.50 (m, 4H).

Workup

  1. temperatureUpon cooling
  2. stirringthe mixture was stirred for 1 h
  3. filtrationthe resulting white solid was collected by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-711cb80480d649cd86fe382827d7ed13
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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