2,3,4,5-Tetrahydro-1-(1-naphthalenylcarbonyl)-1h-1,4-benzodiazepine → HCID 178478880, compound

HRID 849392Notes

Reaction equation

HRID 849392 reaction equation
[ClH:1].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][C:14]3[N:15]=[CH:16][NH:17][CH:18]=3)[CH2:11][CH2:10][N:9]([C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=[O:20])[CH2:8][C:7]=2[CH:31]=1.C1(C(N2C3C=CC=CC=3CNCC2)=O)C2C(=CC=CC=2)C=CC=1.Cl.N1C=C(CN2C3C=CC=CC=3CN(C(C3C4C(=CC=CC=4)C=CC=3)=O)CC2)N=C1>C(Cl)Cl>[ClH:1].[ClH:1].[Br:2][C:3]1[CH:31]=[CH:7][C:8]2[N:9]([C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=[O:20])[CH2:10][CH2:11][N:12]([CH2:13][C:14]3[N:15]=[CH:16][NH:17][CH:18]=3)[CH2:6][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 105662832,3,4,5-Tetrahydro-1-(1-naphthalenylcarbonyl)-1h-1,4-benzodiazepine2×HCID 1784796677-Bromo-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepine, hydrochloride3×HCID 178479669HCID 178479669, compound

Product 1

HCID 178478880HCID 178478880, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Example 42 was prepared as an off white solid from 7-bromo-1,4-benzodiazepine (prepared as described in Compound B of Example 11) using the following procedure: Compound A of Example 4; Compound B of Example 4; Compound C of Example 4; Compound D of Example 1, using methylene chloride as solvent, purification by prep HPLC (YMC S5 ODS 30×250 mm; gradient elution with 0 to 100% buffer B over 45 min; buffer A=MeOH:H2O:TFA (10:90:0.1); buffer B=MeOH:H2O:TFA (90:10:0.1); 25 mL/min) and conversion to the HCl salt by lyophilization from 1M HCl.

Workup

  1. custompurification by prep HPLC (YMC
  2. washgradient elution with 0 to 100% buffer B over 45 min

Sources & evidence

ORD record
ord-c987e10a173f4e0e9a851a42ceb04421
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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