Piperidine → HCID 23659298, compound

HRID 1435410Notes

Reaction equation

HRID 1435410 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CN(C1C=CN=CC=1)C.CC#N>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659298HCID 23659298, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (61 mg, 0.17 mmol), piperidine (0.2 mL, 2.0 mmol) and DMAP (50 mg, 0.41 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 31 mg (45%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.40 (m, 2 H), 1.47-1.64 (m, 8 H), 1.65 (s, 9 H), 2.25-2.48 (m, 1 H), 2.92-3.05 (m, 4 H), 3.29-3.39 (m, 2 H), 3.88-3.98 (m, 2 H), 4.50 (d, J=7.62 Hz, 2 H), 7.82 (dd, J=8.69, 1.66 Hz, 1 H), 8.01 (d, J=8.79 Hz, 1 H), 8.06 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=420.0; Anal. Calcd for C22H33N3O3S+1.10 TFA+0.50H2O+0.10 CH3OH (557.23): C, 52.38; H, 6.42; N, 7.54. Found: C, 52.38; H, 6.43; N, 7.58.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-981c13b3c8f94a028666274c9a4f47f7
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…