2,3,4,5-tetrahydro-1H-1,5-benzodiazepine → HCID 22312679, compound

HRID 133265Notes

Reaction equation

HRID 133265 reaction equation
[N:1]([CH:4]1[C:10](=[O:11])[N:9]([CH2:12][CH:13]2[CH2:15][CH2:14]2)[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[N:6]([CH2:20][CH:21]2[CH2:23][CH2:22]2)[C:5]1=[O:24])=[N+]=[N-].N1C2C=CC=CC=2NCCC1>>[NH2:1][CH:4]1[C:10](=[O:11])[N:9]([CH2:12][CH:13]2[CH2:15][CH2:14]2)[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[N:6]([CH2:20][CH:21]2[CH2:22][CH2:23]2)[C:5]1=[O:24]

Participants

3

Reactant 2

HCID 5771922,3,4,5-tetrahydro-1H-1,5-benzodiazepineHCID 223122573-Azido-2,4-dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Product 1

HCID 22312679HCID 22312679, compound

Conditions

Temperature
-23 °C

Procedure

Following General Procedure 8-L using the product from Step B, 3-amino-2,4-dioxo-1,5-bis-cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine was prepared as a white solid. Purification was by flash chromatography eluting with CH2Cl2/MeOH (98:2 gradient to 95:5, with 5% NH3 in the MeOH) followed by recrystallization from warm CH2Cl2/hexanes (1:1) to −23° C.

Workup

  1. customwas prepared as a white solid
  2. customPurification
  3. washeluting with CH2Cl2/MeOH (98:2 gradient to 95:5
  4. customwith 5% NH3 in the MeOH) followed by recrystallization

Sources & evidence

ORD record
ord-daefbfbb18364f409a9946b7f6f61661
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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