N-{[(5R)-16-(Dimethylamino)-4-oxo-2,3,15,17,18-pentaazabicyclo[12.3.1]octadeca-1(18),10,14,16-tetraen-5-yl]methyl}-N-benzoxyformamide → N-{[(5R)-16-(Dimethylamino)4-oxo-2,3,15,17,18-pentaazabicyclo[12.3.1]octadeca-1(18),14,16-trien-5-yl]methyl}-N-hydroxyformamide

HRID 1786122Notes

Reaction equation

HRID 1786122 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1[N:4]=[C:5]2[N:20]=[C:18]([N:19]=1)[NH:17][NH:16][C:15](=[O:21])[C@@H:14]([CH2:22][N:23]([O:26]CC1C=CC=CC=1)[CH:24]=[O:25])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6]2>CO.[Pd]>[CH3:1][N:2]([CH3:34])[C:3]1[N:4]=[C:5]2[N:20]=[C:18]([N:19]=1)[NH:17][NH:16][C:15](=[O:21])[C@@H:14]([CH2:22][N:23]([OH:26])[CH:24]=[O:25])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 86621284N-{[(5R)-16-(Dimethylamino)-4-oxo-2,3,15,17,18-pentaazabicyclo[12.3.1]octadeca-1(18),10,14,16-tetraen-5-yl]methyl}-N-benzoxyformamide

Product 1

HCID 11372389N-{[(5R)-16-(Dimethylamino)4-oxo-2,3,15,17,18-pentaazabicyclo[12.3.1]octadeca-1(18),14,16-trien-5-yl]methyl}-N-hydroxyformamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-{[(5R)-16-(dimethylamino)-4-oxo-2,3,15,17,18-pentaazabicyclo[12.3.1]octadeca-1(18),10,14,16-tetraen-5-yl]methyl}-N-benzoxyformamide (75 mg) in MeOH (15 mL) was added 10% Pd/C (15 mg, 20% w/w). The reaction mixture was subjected to hydrogenation for 3 hours at room temperature. The reaction mixture was then filtered through a pad of Celite, and washed with MeOH (10 mL×2). Removal of the solvent provided the title compound. MH+380.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite
  2. washwashed with MeOH (10 mL×2)
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-7f785d9910ca43b9bfc8a79f71909a1e
Source dataset
uspto-grants-2009_03
Patent number
US07507726B2

Reaction notes

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