Triethylamine → HCID 21993927, compound

HRID 1978547Notes

Reaction equation

HRID 1978547 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[N:13]1[CH:14]=[C:15]2[N:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=13)[S:18][C:17]([C:25]([OH:27])=O)=[CH:16]2.ON1C(=O)CCC1=O.[NH2:36][CH2:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][N:43]([CH2:46][CH2:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:42](=[O:55])[CH2:41]1.C(N(CC)CC)C.N12CCCNC1CCCC=C2>C(#N)C>[C:49]1([CH2:48][CH2:47][CH2:46][N:43]2[CH2:44][CH2:45][N:40]([CH2:39][CH2:38][CH2:37][NH:36][C:25]([C:17]3[S:18][C:19]4[N:24]5[C:15](=[CH:14][N:13]=[C:23]5[CH:22]=[CH:21][CH:20]=4)[CH:16]=3)=[O:27])[CH2:41][C:42]2=[O:55])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-eneHCID 10943925HCID 10943925, compoundHCID 219937654-(3-Aminopropyl)-1-(3-phenylpropyl)-2-piperazinone

Product 1

HCID 21993927HCID 21993927, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.58 g, 8.24 mmol) was added to a stirred suspension of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid (900 mg, 4.12 mmol) and N-hydroxysuccinimide (948 mg, 8.24 mmol) in acetonotrile (10 ml) at room temperature and the mixture was stirred at room temperature for 2 hours. A solution of 4-(3-aminopropan-1-yl)-1-(3-phenylpropan-1-yl)-2-oxopiperazine (1.38 g, 5.01 mmol), triethylamine (459 mg, 4.54 mmol) and 1,8-diazabicyclo[5.4.0]undecene (1.25 g, 8.24 mmol) in acetonitrile (20 ml) was added to the mixture. After stirring at room temperature for 1 day, the reaction mixture was concentrated in vacuo. The residue was dissolved in water and extracted with chloroform. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (60 g) with Ethyl acetate-Methanol (5:1) to give N-[3-[1-(3-phenylpropan-1-yl)-2-oxopiperazin-4-yl]propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide as a purple amorphous powder (978 mg, 50%).

Workup

  1. stirringAfter stirring at room temperature for 1 day
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with chloroform
  5. washThe extract was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel (60 g) with Ethyl acetate-Methanol (5:1)

Sources & evidence

ORD record
ord-72b0ce8bc364493e8d46e0b0d96a774f
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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