1H-pyrazole-4-carbaldehyde → 1-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carbaldehyde

HRID 1435463Notes

Reaction equation

HRID 1435463 reaction equation
[CH3:1][C:2]([C:6]1[N:10]([CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[CH:18]=[CH:19][C:20]([S:22](Cl)(=[O:24])=[O:23])=[CH:21][C:8]=2[N:7]=1)([CH3:5])[CH2:3][CH3:4].[NH:26]1[CH:30]=[C:29]([CH:31]=[O:32])[CH:28]=[N:27]1>CN(C1C=CN=CC=1)C.CC#N>[CH3:1][C:2]([C:6]1[N:10]([CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[CH:18]=[CH:19][C:20]([S:22]([N:26]3[CH:30]=[C:29]([CH:31]=[O:32])[CH:28]=[N:27]3)(=[O:24])=[O:23])=[CH:21][C:8]=2[N:7]=1)([CH3:5])[CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 51306731H-pyrazole-4-carbaldehydeHCID 579373072-tert-pentyl-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d]imidazole-5-sulfonyl chloride

Product 1

HCID 579373411-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carbaldehydeYield 24%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Following the same procedure in Example 1, Step A, using 2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (2.12 g, 5.5 mmol), 1H-pyrazole-4-carbaldehyde (0.48 g, 5.0 mmol) and DMAP (0.73 g, 6.0 mmol) in MeCN (20 mL). The crude product was purified by MPLC using CH2Cl2/EtOAc (1:1) on silica gel to give 0.53 g (24%) of a white solid as the title compound. MS (ESI) (M+H)+=444.92.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-f44babe54a274578a24eab4f1b5810f9
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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