Ethanol → HCID 10022613, compound

HRID 853811Notes

Reaction equation

HRID 853811 reaction equation
[C:1]([O:4][NH:5][C:6](=[NH:32])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[NH:31])[NH:26]OC(=O)C)=[CH:21][CH:20]=3)=[CH:16][CH:17]=2)=[N:9][CH:8]=1)(=[O:3])[CH3:2].C(O)C>C(O)(=O)C.[Pd]>[C:1]([OH:4])(=[O:3])[CH3:2].[C:25]([C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C:15]2[O:14][C:13]([C:10]3[CH:11]=[CH:12][C:7]([C:6]([NH2:32])=[NH:5])=[CH:8][N:9]=3)=[CH:17][CH:16]=2)=[CH:24][CH:23]=1)(=[NH:26])[NH2:31]

Participants

5

Reactant 2

HCID 702EthanolHCID 178476701HCID 178476701, compound

Product 1

HCID 10022613HCID 10022613, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 37 (170 mg, mmol) in glacial acetic acid (8 mL), and ethanol (10 mL) was added 10% palladium on carbon (70 mg). The mixture was placed on Parr hydrogenation apparatus at 50 psi for 4 h at room temperature. The mixture was filtered off through HYFLO. The filtrate was evaporated under reduced pressure and the precipitate was collected and washed with ether to give 38 in 60% yield, mp 213–216° C.dec. 1H nmr (DMSO-d6); δ 1.78 (s, 6H), 6.43 (d, J=3.3 Hz, 1H), 7.23 (d, J=3.3 Hz, 1H), 7.43 (d, J=7.8 Hz, 2H), 7.49–7.73 (m, 3H), 8.17 (d, J=7.8 Hz, 1H), 8.89 (s, 1H). Calcd. for C18H17N5O-2AcOH-3H2O-0.35EtOH: C, 53.50; H, 6.54; N, 13.74. Found C, 53.57; H, 6.51; N, 13.37.

Workup

  1. filtrationThe mixture was filtered off through HYFLO
  2. customThe filtrate was evaporated under reduced pressure
  3. customthe precipitate was collected
  4. washwashed with ether

Sources & evidence

ORD record
ord-af36f96d22de472aae1393684a6a06e8
Source dataset
uspto-grants-2007_08
Patent number
US07256203B2

Reaction notes

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