4-Methylpiperidine → HCID 23659300, compound

HRID 1435412Notes

Reaction equation

HRID 1435412 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].[CH3:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]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:29]3[CH2:30][CH2:31][CH:26]([CH3:25])[CH2:27][CH2:28]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 693814-MethylpiperidineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659300HCID 23659300, compound

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 (72 mg, 0.19 mmol), 4-methylpiperidine (0.2 mL, 168 mg, 1.69 mmol) and DMAP (69 mg, 0.61 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 38 mg (45% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.90 (d, J=5.86 Hz, 3 H), 1.16-1.34 (m, 3 H), 1.49-1.64 (m, 4 H), 1.67 (s, 9 H), 1.67-1.73 (m, 2 H), 2.23-2.32 (m, 2 H), 2.33-2.44 (m, 1 H), 3.31-3.40 (m, 2 H), 3.73-3.82 (m, 2 H), 3.91-3.98 (m, 2 H), 4.52 (d, J=7.42 Hz, 2 H), 7.84 (dd, J=8.79, 1.76 Hz, 1 H), 8.03 (d, J=8.20 Hz, 1 H), 8.08 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=434.0; Anal. Calcd for C23H35N3O3S+1.10 TFA+0.40 CH3OH (571.86): C, 53.77; H, 6.65; N, 7.35. Found: C, 53.76; H, 6.69; N, 7.33.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-f6a8deb67a514c26ba3fd4dcfdab8f5a
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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