Triethylamine → HCID 178527313, compound

HRID 2114059Notes

Reaction equation

HRID 2114059 reaction equation
Cl.C(O[C:5]([C:7]1[CH:8]=[C:9]2[C:15]([C:16]3[CH:20]=[CH:19][O:18][CH:17]=3)=[CH:14][N:13]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:10]2=[N:11][CH:12]=1)=[NH:6])C.[CH:30]([NH:32][NH2:33])=O.CCN(CC)CC>CCO>[C:24]1([S:21]([N:13]2[C:10]3=[N:11][CH:12]=[C:7]([C:5]4[NH:6][CH:30]=[N:32][N:33]=4)[CH:8]=[C:9]3[C:15]([C:16]3[CH:20]=[CH:19][O:18][CH:17]=3)=[CH:14]2)(=[O:22])=[O:23])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12229HydrazinecarboxaldehydeHCID 67051496HCID 67051496, compound

Product 1

HCID 178527313HCID 178527313, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 39 (300 mg, 0.70 mmol), formic hydrazide (209 mg, 3.47 mmol) and Et3N (759 μM, 6.95 mmol) in EtOH (10.4 mL) was heated at 75° C. overnight. After cooling, the solvent was evaporated and the residue purified by silicagel chromatography using 80% ethyl acetate in hexane (gradient elution) then preparative TLC (1 mm plates, EtOAc eluent) to give 40 as a white solid (132.6 mg, 76%); 1H NMR (400 MHz, CDCl3+2 drops CD3OD) δ 6.71 (m, 1H), 7.40-7.70 (m, 5H), 7.84 (s, 1H), 7.93 (t, J=1.0 Hz, 1H), 8.10-8.30 (m, 3H), 8.63 (d, J=2.0 Hz, 1H), 9.10 (bs, NH); MS (CI) m/z 391.9 (MH+), 433.1 (M+MeCN).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customthe residue purified by silicagel chromatography

Sources & evidence

ORD record
ord-dd4773b99aa9437599a0369e1ae53b4b
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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