4-Piperidinecarboxamide → 1-(5-(4-Fluorophenyl)thieno[3,2-b]pyridin-7-yl)-4-piperidinecarboxamide

HRID 378944Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:5]=[C:4]2[CH:15]=[CH:16][S:17][C:3]=12.[NH:18]1[CH2:26][CH2:25][CH:21]([C:22]([NH2:24])=[O:23])[CH2:20][CH2:19]1.C([O-])(=O)C.[Na+]>CN1CCCC1=O.C(OCC)(=O)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[C:4]3[CH:15]=[CH:16][S:17][C:3]3=[C:2]([N:18]3[CH2:26][CH2:25][CH:21]([C:22]([NH2:24])=[O:23])[CH2:20][CH2:19]3)[CH:7]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 7-chloro-5-(4-fluorophenyl)thieno[3,2-b]pyridine (68 mg, 0.26 mmole), isonipecotamide (66 mg, 0.52 mmole), and sodium acetate (21 mg, 0.26 mmole) in 1-methyl-2-pyrrolidone (3 mL) is stirred and heated in an oil bath at 160° C. for about 4 hours. The reaction mixture is then cooled, diluted with ethyl acetate (15 mL) and washed with water (3×15 mL). The organic layer is dried over sodium sulfate, filtered, and concentrated. The residue is recrystalized with ethyl acetate to give 1-(5-(4-fluorophenyl)thieno[3,2-b]pyridin-7-yl)piperidine-4-carboxamide (55 mg, 60% yield) as a white solid product (m.p. 251° C.-253° C.).

Workup

temperatureThe reaction mixture is then cooled
washwashed with water (3×15 mL)
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue is recrystalized with ethyl acetate

Sources & evidence

ORD record: ord-bdaddf13be914cc8ad8254bbaced129a
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297256B1

Reaction notes

Loading…