Chloride → HCID 136395935, compound

HRID 1489521Notes

Reaction equation

HRID 1489521 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9]([NH:11][CH:12]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[NH:14][C:13]2=S)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:30][CH2:31][CH2:32][OH:33].[Cl-]>C1COCC1>[CH:1]1([CH2:7][CH2:8][C:9]([NH:11][CH:12]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[NH:14][C:13]2=[N:30][CH2:31][CH2:32][OH:33])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 312ChlorideHCID 700EthanolamineHCID 19070843HCID 19070843, compound

Product 1

HCID 136395935HCID 136395935, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-cyclohexyl-N-(2,3-dihydro-5-phenyl-2-thioxo-1H-1,4-benzodiazepin-3-yl)propanamide (162 mg, 0.4 mmol), 2-aminoethanol (96 μL, 98 mg, 1.6 mmol) and mereuric chloride (141 mg, 0.52 mmol) in THF (5 mL) was stirred at 55° C. for 1 h. The solvent was evaporated under reduced pressure and the residue was triturated with EtOAc/Hexane. The solid was collected and dried in vacuo to give 3-cyclohexyl-N-[2,3-dihydro-2-(2-hydroxyethylimino)-5-phenyl-1H-1,4-benzodiazepin-3-yl)propanamide as a solid (120 mg, 69%). A sample (90 mg, 0.2 mmol) was dissolved in dichloromethane (7 mL), cooled to 0° C. and methanesulfonyl chloride (19 μL, 28 mg, 2.4 mmol) and diisopropylethylamine (75 μl, 56 mg, 0.43 mmol) were added. The mixture was stirred at 0° C. for 30 min., then at room temperature for 2 h. The solvent was evaporated under reduced pressure, toluene was added and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH (98:2) to give 3-cyclohexyl-N-{2,4-dihydro-6-phenyl-1H-imidazo[1,2-a][1,4]benzodiazepin-4-yl}propanamide as a solid (40 mg, 48%), m.p. 202°-208.5° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was triturated with EtOAc/Hexane
  3. customThe solid was collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-099c274d10164e4f9601892befd3f12f
Source dataset
uspto-grants-1997_10
Patent number
US05679672

Reaction notes

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