Triethylamine → HCID 24752922, compound

HRID 2092140Notes

Reaction equation

HRID 2092140 reaction equation
Cl.NO.CC1[N:6]([C:11]2[N:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([C:28]4[N:33]=[CH:32][C:31]([C:34]5[N:39]=[N:38][C:37]([C:40]([OH:43])([CH3:42])[CH3:41])=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)([CH3:27])[CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=3)=[CH:13][N:12]=2)C(C)=CC=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CCO.O>[NH2:6][C:11]1[N:12]=[CH:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([C:28]3[N:33]=[CH:32][C:31]([C:34]4[N:39]=[N:38][C:37]([C:40]([OH:43])([CH3:41])[CH3:42])=[CH:36][CH:35]=4)=[CH:30][CH:29]=3)([CH3:27])[CH:24]([CH3:25])[CH3:26])=[CH:21][CH:22]=2)=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 24830537HCID 24830537, compound

Product 1

HCID 24752922HCID 24752922, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Hydroxylamine hydrochloride (94.0 mg, 1.350 mmol) was added to a stirred solution of 4e (72.0 mg, 0.135 mmol) and triethylamine (10.0 μL, 0.0730 mmol) in EtOH/water (900 μL of a 2:1 mixture, respectively) at rt, and the resulting mixture was heated at 80° C. for approximately 14 h. After cooling to rt, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 4f. m/z (ES) 455 (MH)+.

Workup

  1. temperatureAfter cooling to rt
  2. extractionextracted three times with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

Sources & evidence

ORD record
ord-743a8d559ff3447fac97ad3eba95b572
Source dataset
uspto-grants-2013_05
Patent number
US08440672B2

Reaction notes

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