1-Iodopropane → HCID 54188565, compound

HRID 1378052Notes

Reaction equation

HRID 1378052 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][CH2:26][C@H:13]4[C:12]=23)[O:5][N:4]=1.C(N(C(C)C)[CH:30]([CH3:32])[CH3:31])C.[CH2:36](I)[CH2:37][CH3:38]>CN(C)C=O>[Cl:22][C:21]1[C:16]2[C:15](=[O:23])[N:14]3[CH2:24][CH2:25][CH2:26][C@H:13]3[C:12]3[N:11]([CH:10]=[N:9][C:8]=3[C:6]3[O:5][N:4]=[C:3]([CH2:2][N:1]([CH2:36][CH2:37][CH3:38])[CH2:31][CH2:30][CH3:32])[N:7]=3)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 81531DiisopropylethylamineHCID 22876576HCID 22876576, compound

Product 1

HCID 54188565HCID 54188565, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.85 g (5 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, 20 ml of N,N-dimethylformamide, 2.14 ml (12.5 mmol) of N-ethyldiisopropylamine and 0.97 ml (10 mmol) of propyl iodide were stirred at 80° overnight. After evaporating the solvent the residue was chromatographed on 210 g of silica gel while eluting with ethyl acetate. There was obtained 0.81 g (36%) of (S)-8-chloro-11,12,13,13a-tetrahydro-1-(3-dipropylaminomethyl-1,2,4-oxadiazol-5-yl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 155°-158°.

Workup

  1. customAfter evaporating the solvent the residue
  2. customwas chromatographed on 210 g of silica gel
  3. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-21a9891a926347caa02fbc6184b0afac
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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