Triethylamine → HCID 54167831, compound

HRID 1281005Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:21])[C@H:16]([CH:18]([CH3:20])[CH3:19])[NH2:17])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.CCN(CC)CC.[C:31]([C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36](O)=[O:37])#[N:32].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][NH:14][C:15](=[O:21])[C@H:16]([CH:18]([CH3:20])[CH3:19])[NH:17][C:36](=[O:37])[C:35]3[CH:39]=[CH:40][CH:41]=[C:33]([C:31]#[N:32])[CH:34]=3)[CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1-(4-chlorobenzyl)-4-{(valylamino)methyl}piperidine (20 mg, 0.059 mmol) in CH2Cl2 (0.60 mL) was treated with Et3N (0.011 mL, 0.077 mmol), m-cyanobenzoic acid (28 mg, 0.071 mmol), EDCI (13 mg, 0.065 mmol) and HOBt (9 mg, 0.065 mmol). The reaction mixture was stirred at 25° C. for 16 h. The resulting solution was diluted with CH2Cl2 (0.75 mL), washed with 2 N aqueous NaOH solution (2×0.75 mL) and dried by filtration through a PTFE membrane. Concentration afforded the 1-(4-chlorobenzyl)-4-[{N-(3-cyanobenzoyl)valyl}aminomethyl]piperidine (compound No. 619) (24.2 mg, 88%) which required no further purification: The purity was determined by RPLC/MS (85%); ESI/MS m/e 467 (M++H, C26H31ClN4O2).

Workup

washwashed with 2 N aqueous NaOH solution (2×0.75 mL)
dry with materialdried by filtration through a PTFE membrane
concentrationConcentration

Sources & evidence

ORD record: ord-f6a6b3016f60448791c621395dd889ea
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451842B1

Reaction notes

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