Bromomethylcyclopropane → 2,4-Dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

HRID 1760106Notes

Reaction equation

HRID 1760106 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4](=[O:13])[CH2:3]1.Br[CH2:15][CH:16]1[CH2:18][CH2:17]1>>[O:13]=[C:4]1[N:5]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[C:2](=[O:1])[CH2:3]1

Participants

3

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 2835341H-1,5-Benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 223124822,4-Dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Procedure

2,4-Dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine was prepared following General Procedure 4-M using the product from Example 4-P, Step A, and (bromomethyl)cyclopropane (Lancaster). Purification was by flash chromatography eluting with EtOAc/hexanes (3:7 gradient to straight EtOAc), then recrystalization from EtOAc/hexanes.

Workup

  1. customPurification
  2. washeluting with EtOAc/hexanes (3:7 gradient to straight EtOAc)
  3. customrecrystalization from EtOAc/hexanes

Sources & evidence

ORD record
ord-7f8aef5c956e438dbe85a24315c859dd
Source dataset
uspto-grants-2005_01
Patent number
US06838455B2

Reaction notes

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