Propargylamine → HCID 10367575, compound

HRID 1085136Notes

Reaction equation

HRID 1085136 reaction equation
[Cl:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]2[NH:6][C:7](=S)[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1.[CH2:31]([NH2:34])[C:32]#[CH:33]>C(O)CCC.CO>[Cl:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]2[N:6]3[C:32]([CH3:33])=[CH:31][N:34]=[C:7]3[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 239041PropargylamineHCID 10479006HCID 10479006, compound

Product 1

HCID 10367575HCID 10367575, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 7,8-dichloro-2,3-dihydro-4-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)phenyl]-1H-[1,5]benzodiazepin-2-thione (452 mg, 1.0 mmol), propargylamine (110 mg, 2.0 mmol) and red mercuric oxide (216 mg, 1.0 mmol) in n-butanol (5 ml) was heated at reflux for 10 hours. The mixture was cooled, diluted with methanol (50 ml) and filtered through Arbocel filter aid. The filtrate was concentrated under reduced pressure, and purified by flash chromatography (eluting with ethyl acetate:methanol=3:1). The product was further purified by trituration with ether to give the title compound as a buff solid, (170 mg, 38%), m.p. 243°-246° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through Arbocel
  5. filtrationfilter aid
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by flash chromatography (eluting with ethyl acetate:methanol=3:1)
  8. customThe product was further purified by trituration with ether

Sources & evidence

ORD record
ord-2de6ba64cd9047009eaff103d80f7c87
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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