Dipropylamine → HCID 21842220, compound

HRID 1418976Notes

Reaction equation

HRID 1418976 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][S:20][C:16]=4[C:15](=[O:21])[N:14]([CH3:22])[CH2:13][C:12]=23)[O:6][CH:7]=1.[CH2:23]([NH:26][CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25]>O1CCCC1>[CH2:23]([N:26]([CH2:2][C:3]1[N:4]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][S:20][C:16]=4[C:15](=[O:21])[N:14]([CH3:22])[CH2:13][C:12]=23)[O:6][CH:7]=1)[CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 21842299HCID 21842299, compound

Product 1

HCID 21842220HCID 21842220, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.167 g (0.000498 mol) of 3-(4-chloromethyl-oxazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]-diazepin-6-one was dissolved in 20 ml of tetrahydrofuran, treated with 1.4 ml (0.0102 mol) of dipropylamine and boiled at reflux for 20 hrs. The solution was completely freed from the solvents, the residue was chromatographed over silica gel with ethyl acetate/ethanol 1:1 as the eluent and recrystallized from diisopropyl ether. There was obtained 0.075 g (38%) of 3-(4-dipropylaminomethyl-oxazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one as white crystals; m.p. 110°-111°.

Workup

  1. temperatureat reflux for 20 hrs
  2. customthe residue was chromatographed over silica gel with ethyl acetate/ethanol 1:1 as the eluent
  3. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-cbb6914a4eb44fe2b61060c66f3b3a2e
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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