Benzoic Acid → HCID 18426172, compound

HRID 2187849Notes

Reaction equation

HRID 2187849 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 a yellow oil which was. purified by preparative TLC (SiO2, 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 a yellow oil which
  6. custompurified by preparative TLC (SiO2, 10% CH3OH—CH2Cl2)

Sources & evidence

ORD record
ord-e8691c2e16174317b349f93d3bc2f726
Source dataset
uspto-grants-2002_06
Patent number
US06410566B1

Reaction notes

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