Piperidine → HCID 66786827, compound

HRID 1947526Notes

Reaction equation

HRID 1947526 reaction equation
[C:1]([O-])([O-:3])=[O:2].[K+].[K+].Cl[CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[S:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:14][C:12]=2[CH:13]=1.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CC#N>[CH:1]([OH:3])=[O:2].[N:28]1([CH2:8][C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[S:20][C:21]5[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=5[N:23]=4)=[CH:14][C:12]=3[CH:13]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 59577775HCID 59577775, compound

Product 1

HCID 66786827HCID 66786827, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of K2CO3 (33 mg, 0.24 mmol) in MeCN (1 mL) was added 2-(2-chloromethyl-benzofuran-5-yloxy)-benzothiazole (27 mg, 0.08 mmol) and piperidine (5 mg, 0.09 mmol) and the reaction mixture was warmed (55° C., 12 h). The reaction mixture was filtered and concentrated and the resultant residue was purified by reverse phase HPLC to afford the title compound (22 mg, 67%). MS (ESI): mass calcd for C21H20N2O2S, 364.1; m/z found 365.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.75 (d, J=8.0, 1H), 7.64 (d, J=8.1, 1H), 7.62-7.55 (m, 2H), 7.40 (dt, J=8.0, 1.3, 1H), 7.35-7.18 (m, 2H), 6.85 (5, 1H), 3.85 (5, 2H), 2.76-2.53 (m, 4H), 1.73-1.60 (m, 4H), 1.56-1.42 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customthe resultant residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ca4b6d67ddbe4520a0ccdb1a8b6eeda5
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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