Benzoic Acid → HCID 18426172, compound

HRID 133620Notes

Reaction equation

HRID 133620 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>ClCCl.C(N(CC)CC)C>[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, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

EDCI (4.7 mg), 1-hydroxybenzotriazole hydrate (3.3 mg), triethylamine (2.5 mg) and benzoic acid (3.0 mg) were added to a dichloromethane (2.5 mL) solution of 1-(4-aminobenzyl)-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (10.1 mg, 0.023 mmol), and the resulting mixture was shaken at 25° C. for 16 hours. The reaction mixture was washed with a 2 M aqueous solution of NaOH (2 mL×2) and brine (1 mL) and then filtered through a PTFE membrane filter. The solvent was evaporated under reduced pressure to thereby provide yellow oil. The obtained yellow oil was purified by preparative TLC (SiO2, 10% methanol/dichloromethane) to afford 1-[4-(benzoylamino)benzyl]-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. 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. washThe reaction mixture was washed with a 2 M aqueous solution of NaOH (2 mL×2) and brine (1 mL)
  2. filtrationfiltered through a PTFE membrane
  3. filtrationfilter
  4. customThe solvent was evaporated under reduced pressure
  5. customto thereby provide yellow oil
  6. customThe obtained yellow oil was purified by preparative TLC (SiO2, 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b7a487560e2b49fb8d9708c0f7074835
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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