Piperidinium acetate → HCID 178463974, compound

HRID 1620546Notes

Reaction equation

[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[CH2:24]([N:26]([CH2:38][CH3:39])[CH2:27][C:28]#[C:29][CH2:30][NH:31][C:32]1[CH2:36][S:35][C:34](=[O:37])[N:33]=1)[CH3:25].C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:36]2/[C:32]([NH:31][CH2:30][C:29]#[C:28][CH2:27][N:26]([CH2:24][CH3:25])[CH2:38][CH3:39])=[N:33][C:34](=[O:37])[S:35]/2)[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (780 mg) in 2-propanol (5 mL) were added 4-{[4-(diethylamino)but-2-yn-1-yl]amino}-1,3-thiazol-2(5H)-one (550 mg) and piperidinium acetate (334 mg) at room temperature. The reaction mixture was stirred at 60° C. for 3 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (640 mg).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-16b7aa5e440d438690a2207350712255
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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