2-(3-Azido-7-Fluoro-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide → 2-(3-Amino-7-Fluoro-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

HRID 1599101Notes

Reaction equation

HRID 1599101 reaction equation
[N:1]([CH:4]1[C:10](=[O:11])[N:9]([CH2:12][C:13]([N:15]([CH:24]([CH3:26])[CH3:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:14])[C:8]2[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:7]=2[N:6]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[C:5]1=[O:38])=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][CH:4]1[C:10](=[O:11])[N:9]([CH2:12][C:13]([N:15]([CH:24]([CH3:26])[CH3:25])[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[O:14])[C:8]2[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:7]=2[N:6]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[C:5]1=[O:38]

Participants

5

Reactant 2

HCID 189295762-(3-Azido-7-Fluoro-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 189295812-(3-Amino-7-Fluoro-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamideYield 56.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 152 mg of 2-(3-azido-7-fluoro-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide in 10 mL of ethyl acetate was combined with 60 mg of palladium on carbon (10 wt %) and hydrogenated under a balloon of hydrogen gas for 16 hrs. The mixture was filtered, evaporated in vacuo and purified on flash grade silica gel using 3:7 methanol/ethyl acetate. The appropriate fractions were combined, evaporated in vacuo and dried under high vacuum to provide 82 mg of the title compound as a foam. Low resolution MS (FAB)m/e 492 (MH+); TLC (silica) 95:5 dichloromethane/methanol Rf=0.30.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo
  3. custompurified on flash grade silica gel using 3:7 methanol/ethyl acetate
  4. customevaporated in vacuo
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-2060f8bcc90a450584945f20c513716a
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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