2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride → 2-tert-Butyl-5-[(3-methyl-1H-pyrazol-1-yl)sulfonyl]-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole

HRID 1435428Notes

Reaction equation

HRID 1435428 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][C:26]1[CH:30]=[CH:29][NH:28][N: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:28]3[CH:29]=[CH:30][C:26]([CH3:25])=[N:27]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chlorideHCID 178428694HCID 178428694, compound

Product 1

HCID 236599072-tert-Butyl-5-[(3-methyl-1H-pyrazol-1-yl)sulfonyl]-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazoleYield 28%

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 (371 mg, 1.0 mmol), 3-methyl-1H-pyrazole (164 mg, 2.0 mmol) and DMAP (367 mg, 3.0 mmol) in MeCN (10 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 116 mg (28%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.39-1.57 (m, 4 H), 1.59 (s, 9 H), 2.17 (s, 3 H), 2.23-2.33 (m, 1 H), 3.27-3.36 (m, 2 H), 3.88 (m, 2 H), 4.42 (d, J=7.62 Hz, 2 H), 6.31 (d, J=2.54 Hz, 1 H), 7.88-7.99 (m, 2 H), 8.18 (d, J=2.73 Hz, 1 H), 8.28 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=416.8.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-1586e74168a448178845c380e9a6b2f1
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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