2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride → HCID 23659707, compound

HRID 1435426Notes

Reaction equation

HRID 1435426 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].[CH:25]1([C:28]2[CH:32]=[CH:31][NH:30][N:29]=2)[CH2:27][CH2:26]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:30]3[CH:31]=[CH:32][C:28]([CH:25]4[CH2:27][CH2:26]4)=[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 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chlorideHCID 178419915HCID 178419915, compound

Product 1

HCID 23659707HCID 23659707, 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 (93 mg, 0.25 mmol), 3-cyclopropyl-1H-pyrazole (54 mg, 0.50 mmol) and DMAP (92 mg, 0.75 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 30 mg (27% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.62-0.75 (m, 2 H), 0.87-0.99 (m, 2 H), 1.43-1.59 (m, 4 H), 1.61 (s, 9 H), 1.81-1.96 (m, 1 H), 2.24-2.42 (m, 1 H), 3.31-3.39 (m, 2 H), 3.91 (m, 2 H), 4.43 (d, J=7.42 Hz, 2 H), 6.18 (d, J=2.73 Hz, 1H), 7.91 (d, J=8.8 Hz, 1 H), 7.95 (dd, J=8.7, 1.5 Hz, 1 H), 8.15 (d, J=2.73 Hz, 1 H), 8.28 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=442.8; Anal. Calcd for C23H30N4O3S+1.10 TFA+0.10H2O (569.31): C, 53.12; H, 5.54; N, 9.83. Found: C, 53.13; H, 5.62; N, 9.76.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-7e46b9450ecb4e2dbdbeae1ae71ce567
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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