1-Methylpiperazine → HCID 10120275, compound

HRID 2053739Notes

Reaction equation

HRID 2053739 reaction equation
[C:1]1([C:11]2[CH:35]=[CH:34][C:14]([C:15]([N:17]3C4C=CC=CC=4CN4[C:28](C(O)=O)=[CH:29][CH:30]=[C:19]4[CH2:18]3)=[O:16])=[CH:13][C:12]=2[CH3:36])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]=1.[CH3:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.[OH:44]N1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C.[CH:60]([N:63]([CH2:67][CH3:68])[CH:64]([CH3:66])[CH3:65])([CH3:62])[CH3:61]>C(OCC)(=O)C>[C:1]1([C:11]2[CH:35]=[CH:34][C:14]([C:15]([N:17]3[C:18]4[CH:19]=[CH:30][CH:29]=[CH:28][C:68]=4[CH2:67][N:63]4[C:64]([C:66]([N:41]5[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]5)=[O:44])=[CH:65][CH:62]=[C:60]4[CH2:61]3)=[O:16])=[CH:13][C:12]=2[CH3:36])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 5

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10299148HCID 10299148, compoundHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 10120275HCID 10120275, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10-[4-(3,4-Dihydro-naphthalen-1-yl)-3-methyl-benzoyl]-10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepine-3-carboxylic acid of Step B (0.150 g, 0.316 mmol), N-methyl piperazine (0.042 mL, 0.379 mmol), 1-hydroxy benzotriazole (0.047 g, 0.348 mmol) and 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.067 g, 0.348 mmol) were combined in amine-free N,N-dimethylformamide (1.3 mL), followed by addition of N,N-diisopropylethyl amine (0.083 mL, 0.474 mmol). The reaction was stirred at room temperature for 12 hours, then diluted with ethyl acetate and washed with water, saturated aqueous sodium bicarbonate and brine. The combined aqueous washings were saturated with sodium chloride and extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 5% methanol in chloroform to afford the title compound (0.170 g) as a white solid.

Workup

  1. washwashed with water, saturated aqueous sodium bicarbonate and brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-acef5a2f199e45d5a04b374a9d572ad4
Source dataset
uspto-grants-2008_02
Patent number
US07326700B2

Reaction notes

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