4-Methylpyrazole → HCID 23659708, compound

HRID 1435427Notes

Reaction equation

HRID 1435427 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:27]=[N:28][NH:29][CH:30]=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:27]=[C:26]([CH3:25])[CH:30]=[N:29]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 34064-MethylpyrazoleHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659708HCID 23659708, 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 (371 mg, 1.0 mmol), 4-methyl-1H-pyrazole (164 mg, 2.0 mmol) and DMAP (366 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 165 mg (40% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.41-1.58 (m, 4 H), 1.61 (s, 9 H), 2.05 (s, 3 H), 2.22-2.47 (m, 1 H), 3.30-3.40 (m, 2 H), 3.91 (m, 2 H), 4.43 (d, J=7.62 Hz, 2 H), 7.60 (s, 1 H), 7.91 (d, J=8.2 Hz, 1 H), 7.95 (dd, J=8.8, 1.8 Hz, 1H), 8.05-8.14 (m, 1 H), 8.28 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=416.8.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-fd67d8d496314e3984a5e4fb13e1ccf0
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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