Pyrazole → HCID 23659491, compound

HRID 1435419Notes

Reaction equation

HRID 1435419 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]=[CH:28][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]=[CH:28][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 1048PyrazoleHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23659491HCID 23659491, 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 (76 mg, 0.20 mmol), pyrazole (34 mg, 0.50 mmol) and DMAP (82 mg, 0.67 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 46 mg (56% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.36-1.54 (m, 4 H), 1.56 (s, 9 H), 2.15-2.41 (m, 1 H), 3.23-3.38 (m, 2 H), 3.88 (m, 2 H), 4.37 (d, J=7.62 Hz, 2H), 6.47 (dd, J=2.73, 1.56 Hz, 1 H), 7.73 (d, J=1.37 Hz, 1 H), 7.77-7.85 (m, 1 H), 7.86-7.94 (m, 1 H), 8.26 (d, J=1.56 Hz, 1 H), 8.30 (d, J=2.73 Hz, 1 H); MS (ESI) (M+H)+=403.0; Anal. Calcd for C20H26N4O3S+0.50 TFA+0.20 EtOAc (477.15): C, 54.88; H, 5.94; N, 11.74. Found: C, 54.78; H, 5.83; N, 11.69.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-445ae8ca3ba0401993536b337f1e019e
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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