Acetohydrazide → HCID 89610466, compound

HRID 1507727Notes

Reaction equation

HRID 1507727 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([O:32][C:33]1[C:37]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:36]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[N:35]([C:51]2[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][CH:52]=2)[C:34]=1[C:59]([O-])=[O:60])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([NH+](CC)CC)C.CCN(C(C)C)C(C)C.[C:78]([NH:81][NH2:82])(=[O:80])[CH3:79]>CN(C=O)C>[C:78]([NH:81][NH:82][C:59]([C:34]1[N:35]([C:51]2[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][CH:52]=2)[C:36]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[C:37]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:33]=1[O:32][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:60])(=[O:80])[CH3:79]

Participants

6

Reactant 4

HCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89610545HCID 89610545, compound

Product 1

HCID 89610466HCID 89610466, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (739 mg, 1.94 mmol) was added to a solution of triethylammonium 3,4-bis(benzyloxy)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (5) (325 mg, 0.65 mmol), DIPEA (566 μL, 3.24 mmol) and acetohydrazide (53 mg, 0.71 mmol) in DMF (5 mL) at 0° C. The mixture was stirred for 30 min and allowed to warm to RT. The reaction was partitioned between water (10 mL) and Et2O (30 mL) and NH4OAc (aq.) (20 mL) was added, the organic layer was separated and washed with sat. NaHCO3 (aq.) (20 mL), brine (20 mL), dried (MgSO4), filtered and solvents removed in vacuo. The product was purified by silica gel chromatography (40 g, 0-80% EtOAc in isohexane) to afford ethyl 5-(2-acetylhydrazinecarbonyl)-3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (31) (196 mg, 100%) as a colourless oil: m/z 558 (M+H)+ (ES+).

Workup

  1. customThe reaction was partitioned between water (10 mL) and Et2O (30 mL) and NH4OAc (aq.) (20 mL)
  2. additionwas added
  3. customthe organic layer was separated
  4. washwashed with sat. NaHCO3 (aq.) (20 mL), brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvents removed in vacuo
  8. customThe product was purified by silica gel chromatography (40 g, 0-80% EtOAc in isohexane)

Sources & evidence

ORD record
ord-c5bc4e4110254a72b4d7df14a0f893cc
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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