1-(2-Chloroethyl)-4-methylpiperazine → 6,7-difluoro-2.9-dihydro-2-[2-(4-methylpiperazino)ethyl]-9-[(dipropylamino)acetyl]-3H-pyrido[3,2-c]-s-triazolo[4,3-a][1,5]-benzodiazepin-3-one

HRID 1658795Notes

Reaction equation

HRID 1658795 reaction equation
[F:1][C:2]1[C:30]([F:31])=[CH:29][C:5]2[N:6]([C:19](=[O:28])[CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])[C:7]3[N:18]=[CH:17][CH:16]=[CH:15][C:8]=3[C:9]3[N:10]([C:11](=[O:14])[NH:12][N:13]=3)[C:4]=2[CH:3]=1.[Na].[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41]Cl)[CH2:36][CH2:35]1>CN(C)C=O.C1(C)C(C)=CC=CC=1>[F:1][C:2]1[C:30]([F:31])=[CH:29][C:5]2[N:6]([C:19](=[O:28])[CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])[C:7]3[N:18]=[CH:17][CH:16]=[CH:15][C:8]=3[C:9]3[N:10]([C:11](=[O:14])[N:12]([CH2:41][CH2:40][N:37]4[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]4)[N:13]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 4137911-(2-Chloroethyl)-4-methylpiperazineHCID 5360545SodiumHCID 215255736,7-difluoro-2,9-dihydro-9-[(dipropylamino)acetyl]-3H-pyrido[3,2-c]-s-triazolo[4,3-a][1,5]benzodiazepin-3-one

Product 1

HCID 215255366,7-difluoro-2.9-dihydro-2-[2-(4-methylpiperazino)ethyl]-9-[(dipropylamino)acetyl]-3H-pyrido[3,2-c]-s-triazolo[4,3-a][1,5]-benzodiazepin-3-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7237O-XyleneSolvent

Procedure

In the manner given in Example 25, to 6,7-difluoro-2,9-dihydro-9-[ (dipropylamino)acetyl]-3H-pyrido[3,2-c]-s-triazolo[4,3-a][1,5]benzodiazepin-3-one in dimethylforamide is added a solution of sodium hydrided in mineral oil. The mixture is allowed to react at about 95°C. for 40 minutes and after cooling [2-(4-methylpiperazino)-ethyl]chloride in xylene is added. The mixture is kept at 95°-100° C. for a period of 22 hours, evaporated and worked up as in example 25 to give 6,7-difluoro-2.9-dihydro-2-[2-(4-methylpiperazino)ethyl]-9-[(dipropylamino)acetyl]-3H-pyrido[3,2-c]-s-triazolo[4,3-a][1,5]-benzodiazepin-3-one.

Workup

  1. customto react at about 95°C. for 40 minutes
  2. additionis added
  3. customevaporated

Sources & evidence

ORD record
ord-161c44bd60e24521a452968604c4c140
Source dataset
uspto-grants-1976_06
Patent number
US03966736

Reaction notes

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