Triethylamine → HCID 10184740, compound

HRID 584976Notes

Reaction equation

HRID 584976 reaction equation
Cl.[CH3:2][N:3](C)[CH2:4]CCN=C=NCC.[C:13]([NH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=1)(=[O:15])[CH3:14].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.CN[C:45]1[CH:46]=[C:47]([C:51]2[CH:56]=[CH:55][C:54]([CH:57](C)[CH:58]3[S:62][C:61](=[O:63])[NH:60][C:59]3=[O:64])=[CH:53][CH:52]=2)[CH:48]=[CH:49][CH:50]=1>ClCCl>[C:13]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([N:3]([CH2:4][C:45]2[CH:46]=[C:47]([C:51]3[CH:52]=[CH:53][C:54]([CH2:57][CH:58]4[S:62][C:61](=[O:63])[NH:60][C:59]4=[O:64])=[CH:55][CH:56]=3)[CH:48]=[CH:49][CH:50]=2)[CH3:2])=[O:23])=[CH:24][CH:25]=1)(=[O:15])[CH3:14]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 19266p-Acetamidobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86591269HCID 86591269, compound

Product 1

HCID 10184740HCID 10184740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

320 mg (1.7 mmol) of 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride are added portionwise, at 0° C., to a solution of 270 mg (1.5 mmol) of 4-acetamidobenzoic acid, 230 μl (1.6 mmol) of triethylamine, 230 mg (1.7 mmol) of 1-hydroxybenzo-triazole and 500 mg (1.5 mmol) of 5-(3′-methylamino-methylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione in 5 ml of dichloromethane. The reaction medium is stirred at from 0° C. to room temperature for 18 hours, washed with saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 99/1 dichloromethane/methanol mixture. After evaporation of the solvents, 600 mg (80%) of 4-acetylamino-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbenzamide are obtained in the form of a white solid with a melting point of 207° C.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution
  2. extractionextracted with dichloromethane
  3. customThe organic phase is separated out
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 99/1 dichloromethane/methanol mixture
  10. customAfter evaporation of the solvents, 600 mg (80%) of 4-acetylamino-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbenzamide
  11. customare obtained in the form of a white solid with a melting point of 207° C.

Sources & evidence

ORD record
ord-46a0b8fe21a546ba83ec5c419c62077b
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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