Piperidine → HCID 49833910, compound

HRID 1947530Notes

Reaction equation

HRID 1947530 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]2[CH:8]=[C:9]([O:12][C:13]3[S:14][C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)[CH:10]=[CH:11][C:5]=2[CH:4]=1.CCN(C(C)C)C(C)C.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>CC#N>[N:31]1([CH2:2][C:3]2[S:7][C:6]3[CH:8]=[C:9]([O:12][C:13]4[S:14][C:15]5[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=5[N:17]=4)[CH:10]=[CH:11][C:5]=3[CH:4]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 595776262-(2-Chloromethyl-benzo[b]thiophen-6-yloxy)-benzothiazole

Product 1

HCID 49833910HCID 49833910, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution 2-(2-chloromethyl-benzo[b]thiophen-6-yloxy)-benzothiazole (86 mg, 0.26 mmol) in MeCN (3 mL) was added DIEA (0.014 mL, 11 mg, 0.8 mmol) followed by piperidine (0.051 mL, 44 mg, 0.52 mmol) and stirred (rt, 12 h). The reaction mixture was partitioned between DCM (15 mL) and saturated NaHCO3(5 mL). The organic layer was washed with saturated NH4Cl (10 mL), dried, filtered and concentrated in vacuo. The resulting residue was purified by reverse phase chromatography to provide the title compound as colorless solid (48 mg, 49%). MS (ESI): mass calcd. for C21H20N2OS2, 380.1; m/z found, 381.1[M+H]+. 1H NMR (400 MHz, CDCl3): 7.79 (d, J=2.3, 1H), 7.75-7.72 (m, 1H), 7.70 (d, J=8.6, 1H), 7.65 (dd, J=8.0, 0.7, 1H), 7.40-7.35 (m, 1H), 7.29 (dd, J=8.6, 2.3, 1H), 7.28-7.21 (m, 1H), 7.13 (5, 1H), 3.75 (5, 2H), 2.55-2.40 (m, 4H), 1.69-1.54 (m, 4H), 1.52-1.32 (m, 2H).

Workup

  1. customThe reaction mixture was partitioned between DCM (15 mL) and saturated NaHCO3(5 mL)
  2. washThe organic layer was washed with saturated NH4Cl (10 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-ff94ec34dec24655ac708b97741f3dd5
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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