Ethylamine → HCID 15231170, compound

HRID 1034413Notes

Reaction equation

HRID 1034413 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=2[N:12]2[CH:20]=[N:21][C:22]([C:23]([OH:25])=O)=[C:11]2[CH2:10][N:9]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:32]([NH2:34])[CH3:33].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=2[N:12]2[CH:20]=[N:21][C:22]([C:23]([NH:34][CH2:32][CH3:33])=[O:25])=[C:11]2[CH2:10][N:9]=1

Participants

6

Reactant 4

HCID 6341EthylamineHCID 10340Sodium CarbonateHCID 24819Phosphorus pentachlorideHCID 15292435HCID 15292435, compound

Product 1

HCID 15231170HCID 15231170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.4 g (1 mmol) of 6-(2-bromophenyl)-8-fluoro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, 50 mL of methylene chloride and 0.3 g (1.44 mmol) of phosphorus pentachloride was stirred at room temperature for 2.5 hours. Ethylamine was introduced until the reaction mixture was basic. It was layered with 10% aqueous sodium carbonate solution and the two phases were stirred for 15 minutes The organic layer was separated, dried and evaporated. The residue was crystallized from ethyl acetate/hexane to yield 0.37 g of product having the above formula. For analysis it was recrystallized from ethanol to leave colorless crystals with m.p. 218°-220° C.

Workup

  1. stirringthe two phases were stirred for 15 minutes The organic layer
  2. customwas separated
  3. customdried
  4. customevaporated
  5. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-947a8b8a7ed84c42bdb9621e1bd3bf53
Source dataset
uspto-grants-1994_05
Patent number
US05317018

Reaction notes

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