N-Methylaniline → 2-tert-Butyl-N-methyl-N-phenyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonamide

HRID 1435420Notes

Reaction equation

HRID 1435420 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][NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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:26]([CH3:25])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH: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 7515N-MethylanilineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 236594922-tert-Butyl-N-methyl-N-phenyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonamide

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 (132 mg, 0.36 mmol), N-methylaniline (0.1 mL, 99 mg, 0.92 mmol) and DMAP (120 mg, 0.98 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (4:1) on silica gel to give 59 mg (38% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.42-1.60 (m, 4 H), 1.63 (s, 9 H), 2.24-2.43 (m, 1 H), 3.19 (s, 3 H), 3.28-3.41 (m, 2 H), 3.92 (m, 2 H), 4.48 (d, J=7.42 Hz, 2 H), 7.03-7.12 (m, 2 H), 7.20-7.35 (m, 3 H), 7.60 (dd, J=8.79, 1.76 Hz, 1 H), 7.82 (d, J=1.17 Hz, 1 H), 7.94 (d, J=8.79 Hz, 1 H); MS (ESI) (M+H)+=442.0; Anal. Calcd for C24H31N3O3S+1.00 TFA+0.20 EtOAc+0.10H2O (575.04): C, 55.98; H, 5.92; N, 7.31. Found: C, 55.89; H, 5.87; N, 7.30.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-fd1e707846464a3c838ef8a3fbdbee96
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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