HCID 22288337, compound → HCID 22288236, compound

HRID 968259Notes

Reaction equation

HRID 968259 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[N:4]=[CH:3]1.[H][H]>C(O)(=O)C.[Pd].[Zn]>[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][CH2:3]1

Participants

6

Reactant 2

HCID 22288337HCID 22288337, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22288236HCID 22288236, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Reduction of intermediate 21 using, for example, zinc dust in glacial acetic acid then provides 3-amino-1,3-dihydro-1,5-benzodiazepin-2-one 22. This reaction is typically conducted at ambient temperature for about 0.5 to about 6 hours. Alternatively, intermediate 21 can be reduced with hydrogen using a catalyst, such as palladium on carbon, to afford 3-amino-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one 23. Typically, this reaction is conducted at ambient temperature for about 12 to about 48 hours. If desired, compounds 22 and 23 can then be coupled with an amino acid derivative using the procedures described herein.

Workup

  1. waitThis reaction is typically conducted at ambient temperature for about 0.5 to about 6 hours

Sources & evidence

ORD record
ord-576937c5cef940648a37e0bb9b240ed0
Source dataset
uspto-grants-2005_10
Patent number
US06958330B1

Reaction notes

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