1H-pyrazole-4-carbaldehyde → HCID 23659910, compound

HRID 1435431Notes

Reaction equation

HRID 1435431 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].[NH:25]1[CH:29]=[C:28]([CH:30]=[O:31])[CH:27]=[N:26]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:25]3[CH:29]=[C:28]([CH:30]=[O:31])[CH:27]=[N:26]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 51306731H-pyrazole-4-carbaldehydeHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659910HCID 23659910, compoundYield 30%

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 (3.26 g, 8.8 mmol), 1H-pyrazole-4-carbaldehyde (1.01 g, 10.5 mmol) and DMAP (2.15 g, 17.6 mmol) in MeCN (70 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 1.12 g (30%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.39-1.56 (m, 4 H), 1.58 (s, 9 H), 2.21-2.36 (m, 1 H), 3.29-3.33 (m, 2 H), 3.88 (m, 2 H), 4.40 (d, J=7.42 Hz, 2 H), 5.41 (s, 1 H), 7.69 (s, 1 H), 7.84-7.90 (m, 1 H), 7.92-7.97 (m, 1 H), 8.25 (t, J=0.68 Hz, 1 H), 8.29 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=430.7; Anal. Calcd for C21H26N4O4S+0.80 TFA+0.30 CH3CN+0.20H2O (537.67): C, 51.83; H, 5.27; N, 11.20. Found: C, 51.79; H, 5.20; N, 11.16.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-593a3a3b4c0643d6b23b60a508de9c59
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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