Formic Acid → HCID 178492388, compound

HRID 343216Notes

Reaction equation

HRID 343216 reaction equation
C([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18]2([O:52][CH3:53])[C:24](=[O:25])[N:23]([CH2:26][C:27]([N:29]([CH:38]([CH3:40])[CH3:39])[C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[O:28])[C:22]3[CH:41]=[CH:42][CH:43]=[CH:44][C:21]=3[N:20]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:19]2=[O:51])=[N:9]1)C1C=CC=CC=1.C(O)=O>C(O)C.[Pd]>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18]2([O:52][CH3:53])[C:24](=[O:25])[N:23]([CH2:26][C:27]([N:29]([CH:38]([CH3:39])[CH3:40])[C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[O:28])[C:22]3[CH:41]=[CH:42][CH:43]=[CH:44][C:21]=3[N:20]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:19]2=[O:51])=[N:9]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 67700001HCID 67700001, compound

Product 1

HCID 178492388HCID 178492388, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirring solution of 80 mg (0.11 mmol) of 2-[3-(1-benzyl-1H-Indazol-3-ylmethyl)-3-methoxy-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl) acetamide in 10 mL of a 10% solution of formic acid in absolute ethanol is added 70 mg of 10% palladium on carbon. The resulting black suspension is heated at reflux for 6 h, and then cooled to RT. The reaction mixture is filtered through Celite to remove the catalyst and the solvent removed in vacuo. Purification of the residue via silica gel MPLC using an Si60 column and hexane/EtOAc 1/1 as eluent followed by lyophilization afforded 41 mg of the title compound as a white amorphous solid: 1H NMR (DMSO-d6, 300 MHz) δ7.83 (d, 1H, J=8.3), 7.38-6.94 (m, 16H), 6.59 (d, 1H, J=7.1), 4.76 (m, 1H), 4.19 (s, br, 2H), 3.85 (d, 1H), J=15.7), 3.73 (m, 4H), 2.88 (s, 3H), 0.93 (m, 6H); low resolution MS (FAB)m/e 618 (MH+).

Workup

  1. temperatureThe resulting black suspension is heated
  2. temperatureat reflux for 6 h
  3. filtrationThe reaction mixture is filtered through Celite
  4. customto remove the catalyst
  5. customthe solvent removed in vacuo
  6. customPurification of the residue via silica gel MPLC

Sources & evidence

ORD record
ord-7b93959675cb4471931a34c4900003bb
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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