Ammonia → HCID 18426204, compound
Reaction equation
CC[N:3]=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1.N.O1CCOCC1.[C:30]([C:33]1[CH:34]=[C:35]([CH:61]=[CH:62][CH:63]=1)[CH2:36][N:37]1[CH2:42][CH2:41][CH:40]([CH2:43][NH:44][C:45](=[O:60])[CH2:46][NH:47][C:48](=[O:59])[C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([C:55]([F:58])([F:57])[F:56])[CH:50]=2)[CH2:39][CH2:38]1)(O)=[O:31]>CN(C=O)C.C(Cl)(Cl)Cl.CCN(CC)CC>[C:30]([C:33]1[CH:34]=[C:35]([CH:61]=[CH:62][CH:63]=1)[CH2:36][N:37]1[CH2:42][CH2:41][CH:40]([CH2:43][NH:44][C:45](=[O:60])[CH2:46][NH:47][C:48](=[O:59])[C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([C:55]([F:58])([F:57])[F:56])[CH:50]=2)[CH2:39][CH2:38]1)(=[O:31])[NH2:3]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
EDCI (10.7 mg), 1-hydroxybenzotriazole hydrate (7.5 mg), Et3N (15.4 mg), 0.5 M NH3 in dioxane (0.1 mL, 0.05 mmol) and DMF (0.5 mL) were added to a solution of 1-(3-carboxybenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (19.4 mg, 0.041 mmol) in CHCl3 (2.5 mL). The reaction mixture was stirred at 25° C. for 20 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 1-(3-carbamoylbenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (compound No. 924) as a pale yellow solid (17.9 mg, 92%): The purity was determined by RPLC/MS (89%); ESI/MS m/e 447.3 (M++H, C24H27F3N4O3).
Workup
- washwashed with 2 N aqueous NaOH (2×2 mL) and brine (1 mL)
- filtrationAfter filtration through PTFE membrane
- filtrationfilter
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-1f318f8afda54e1490add8a257d76d4f
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362177B1
Reaction notes
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