Triethylamine → HCID 21993682, compound

HRID 1978533Notes

Reaction equation

HRID 1978533 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]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][C:41]1=[O:53].C(N(CC)CC)C>C(#N)C>[C:49]([O:48][C:46]([N:43]1[CH2:44][CH2:45][N:40]([CH2:39][CH2:38][CH2:37][NH:36][C:25]([C:17]2[S:18][C:19]3[N:24]4[C:15](=[CH:14][N:13]=[C:23]4[CH:22]=[CH:21][CH:20]=3)[CH:16]=2)=[O:27])[C:41](=[O:53])[CH2:42]1)=[O:47])([CH3:52])([CH3:50])[CH3:51]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compoundHCID 21993633HCID 21993633, compound

Product 1

HCID 21993682HCID 21993682, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.22 g, 22.0 mmol) was added to a stirred suspension of 5-thia-1,8b-diazaacenaphtylene-4-carboxylic acid (2.40 g, 11.0 mmol) and N-hydroxysuccinimide (2.53 g, 22.0 mmol) in acetonotrile (30 ml) at room temperature and the mixture was stirred at room temperature for 1.5 hours. A solution of 1-(3-aminopropan-1-yl)-4-tert-butoxycarbonyl-2-oxopiperazine (3.67 g, 14.3 mmol) and triethylamine (4.45 g, 44.0 mmol) in acetonitrile (15 ml) was added to the mixture. After stirring at room temperature for 19 hours, 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 (50 g) with Ethyl acetate-Methanol (10:1) to give N-[3-(4-tert-butoxycarbonyl-2-oxopiperazin-1-yl)propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide as a purple amorphous powder(1.53 g, 30%).

Workup

  1. stirringAfter stirring at room temperature for 19 hours
  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 (50 g) with Ethyl acetate-Methanol (10:1)

Sources & evidence

ORD record
ord-7ca22999ee134a7bb4ba1003195b69b3
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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