Hydrazine → HCID 20663658, compound

HRID 1067159Notes

Reaction equation

HRID 1067159 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[B:11]([OH:13])O)=O.[Cl:14][C:15]1[CH:29]=[CH:28][C:18]([CH2:19][N:20]2[C:24](=[O:25])[CH2:23][N:22]=[C:21]2[NH:26][NH2:27])=[CH:17][CH:16]=1.NN>C(O)C.CC(O)=O>[Cl:14][C:15]1[CH:29]=[CH:28][C:18]([CH2:19][N:20]2[C:24](=[O:25])[CH2:23][N:22]=[C:21]2[N:26]2[N:27]=[CH:1][C:3]3[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=3[B:11]2[OH:13])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 9321HydrazineHCID 27343652-Formyl-4-methoxybenzeneboronic acidHCID 2782121HCID 2782121, compound

Product 1

HCID 20663658HCID 20663658, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1 (360 mg, 2.0 mmol) and 3-(4-chlorobenzyl)-2-hydrazino-3,5-dihydroimidazol-4-one (compound 16, commercially available from Maybridge Chemical Co., Ltd., Ryan Scientific #RF03409; 500 mg, 2.1 mmol) in 6 mL of absolute ethanol was treated with 1 drop of AcOH and was warmed on a steam bath until homogeneous. The mixture was allowed to stand at 23 ° C. overnight, whereupon the 137 mg of the starting hydrazine that had separated as crystals (mp 186-188° C.) was removed by suction filtration. The filtrate was rotary evaporated to dryness, and the residue was triturated with Et2O to give 528 mg (69%, 91% based on unrecovered hydrazine) of the methoxy precursor (compound 17) as a pale yellow powder: mp 135-145° C. (EtOH). 1H NMR ((CD3)2SO) δ 9.16 (s, exchanges with D2O, 1, OH), 7.62 (d, J=8.4 Hz, 1), 7.40 (d, J =8.5 Hz, 2, p-CICA), 7.32 (d, J=8.5 Hz, 2, p-ClC6H4), 7.12 (m, 3), 6.97 (d, J=8.0 Hz, 1), 6.85 (d, J =8.0 Hz, 1), 6.68 (s, 1), 4.23 (d, J=5.6 Hz, 2, benzyl-CH2), 3.67 (s, 3, OCH3). Low-resolution DCI mass spectrum, m/z 383 (2%, MH+). Deprotection of 17 can be effected using conventional techniques to form 18.

Workup

  1. temperaturewas warmed on a steam bath until homogeneous
  2. customhad separated as crystals (mp 186-188° C.)
  3. customwas removed by suction filtration
  4. customThe filtrate was rotary evaporated to dryness
  5. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-b6ad1c9a1309443eb1293fea6d16b1ce
Source dataset
uspto-grants-2001_06
Patent number
US06248305B1

Reaction notes

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