Benzoic Acid → HCID 18426172, compound

HRID 1281034Notes

Reaction equation

HRID 1281034 reaction equation
CCN=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1.[C:23](O)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[NH2:32][C:33]1[CH:63]=[CH:62][C:36]([CH2:37][N:38]2[CH2:43][CH2:42][CH:41]([CH2:44][NH:45][C:46](=[O:61])[CH2:47][NH:48][C:49](=[O:60])[C:50]3[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=3)[CH2:40][CH2:39]2)=[CH:35][CH:34]=1>C(Cl)Cl.CCN(CC)CC>[C:23]([NH:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:37][N:38]2[CH2:43][CH2:42][CH:41]([CH2:44][NH:45][C:46](=[O:61])[CH2:47][NH:48][C:49](=[O:60])[C:50]3[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:57])[F:58])[CH:51]=3)[CH2:40][CH2:39]2)=[CH:62][CH:63]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18426266HCID 18426266, compound

Product 1

HCID 18426172HCID 18426172, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

EDCI (4.7 mg), 1-hydroxybenzotriazole hydrate (3.3 mg), Et3N (2.5 mg) and benzoic acid (3.0 mg) were added to a solution of 1-(4-aminobenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (10.1 mg, 0.023 mmol) in CH2Cl2 (2.5 mL). The reaction mixture was stirred at 25° C. for 16 h, washed with 2 N aqueous NaOH (2×2 mL) and brine (1 mL). After filtration through PTFE membrane filter, the solvent was removed under reduced pressure to afford an yellow oil which was purified by preparative TLC (SiO3, 10% CH3OH—CH2Cl2) to give 1-(4-(benzoylamino)benzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (compound No. 519) as a colorless oil (4.6 mg, 36%): The purity was determined by RPLC/MS (99%); ESI/MS m/e 553.2 (M++H, C30H31F3N4O3).

Workup

  1. washwashed with 2 N aqueous NaOH (2×2 mL) and brine (1 mL)
  2. filtrationAfter filtration through PTFE membrane
  3. filtrationfilter
  4. customthe solvent was removed under reduced pressure
  5. customto afford an yellow oil which
  6. customwas purified by preparative TLC (SiO3, 10% CH3OH—CH2Cl2)

Sources & evidence

ORD record
ord-818ea093c7a640cdba39ac096fbc2405
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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