N-Hydroxysuccinimide → HCID 21993721, compound

HRID 1978485Notes

Reaction equation

HRID 1978485 reaction equation
[N:1]1[CH:2]=[C:3]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[S:6][C:5]([C:13]([OH:15])=O)=[CH:4]2.ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[NH2:38][CH2:39][C:40]1[CH:58]=[CH:57][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH2:47][CH2:46]2)=[CH:42][CH:41]=1.C1CCN2C(=NCCC2)CC1>C(#N)C.C(N(CC)CC)C>[C:51]1([CH:48]2[CH2:47][CH2:46][N:45]([CH2:44][C:43]3[CH:57]=[CH:58][C:40]([CH2:39][NH:38][C:13]([C:5]4[S:6][C:7]5[N:12]6[C:3](=[CH:2][N:1]=[C:11]6[CH:10]=[CH:9][CH:8]=5)[CH:4]=4)=[O:15])=[CH:41][CH:42]=3)[CH2:50][CH2:49]2)[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

8

Reactant 5

HCID 80170N-HydroxysuccinimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compoundHCID 21993962HCID 21993962, compound

Product 1

HCID 21993721HCID 21993721, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a suspension of 1.0 g (4.58 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.90 g (7.82 mM) of N-hydroxysuccinimide in acetonitrile (10 ml) was added 1.51 g (7.88 mM) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide hydrochloride at room temperature, and the mixture was stirred for 1 hour. To this reaction mixture was added a solution of 1.67 g (4.73 mM) of 1-[4-(aminomethyl)benzyl]-4-phenylpiperidine dihydrochloride, 1.44 g (9.46 mM) of DBU, and 0.55 ml (3.95 mM) of triethylamine in acetonitrile (20 ml), and the mixture was further stirred for 4 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with ethyl acetate (a small amount of ethanol was additionally used). The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. This crude product was purified by column chromatography (methanol/ethyl acetate 20-30%) to provide the title compound as red amorphous substance.

Workup

  1. stirringthe mixture was further stirred for 4 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate (a small amount of ethanol
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over MgSO4
  7. customThis crude product was purified by column chromatography (methanol/ethyl acetate 20-30%)

Sources & evidence

ORD record
ord-a01cc535d7e547e8aafde698a047037c
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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