Pyrazole → HCID 57937391, compound

HRID 1435515Notes

Reaction equation

HRID 1435515 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:27]1[CH:31]=[CH:30][CH:29]=[N:28]1>CC#N>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23]([N:27]3[CH:31]=[CH:30][CH:29]=[N:28]3)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1048PyrazoleHCID 579372942-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937391HCID 57937391, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (202 mg, 0.5 mmol) and pyrazol (186 mg, 2.7 mmol) in MeCN (6 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 164 mg (75%) of a white solid as the title compound. 1H NMR (400 MHz, CHLOROFORM-D) δ 1.43-1.54 (m, 1 H), 1.56 (s, 9 H), 1.59-1.80 (m, 4 H), 2.01-2.22 (m, 3 H), 2.49-2.79 (m, 1 H), 4.24 (d, J=7.42 Hz, 2 H), 6.38 (dd, J=2.73, 1.56 Hz, 1 H), 7.43 (d, J=8.59 Hz, 1 H), 7.70 (d, J=0.98 Hz, 1 H), 7.96 (dd, J=8.69, 1.66 Hz, 1 H), 8.15 (d, J=2.73 Hz, 1 H), 8.40 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=437.3; Anal. Calcd for C21H26F2N4O2S+0.2H2O (440.13): C, 57.31; H, 6.05; N, 12.73. Found: C, 57.23; H, 6.05; N, 12.83.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-94083c1931ab4dbb83291401d3a2f2d2
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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