2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride → HCID 23659908, compound

HRID 1435429Notes

Reaction equation

HRID 1435429 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][C:27]([NH:30]C(=O)OC(C)(C)C)=[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][C:27]([NH2:30])=[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 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chlorideHCID 178452885HCID 178452885, compound

Product 1

HCID 23659908HCID 23659908, compoundYield 19%

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 (1.46 g, 3.93 mmol), tert-butyl 1H-pyrazol-3-ylcarbamate (0.80 g, 4.33 mmol) (see following step B for preparation), and DMAP (1.47 g, 12.0 mmol) in MeCN (40 mL). The crude product was purified by MPLC using EtOAc on silica gel to give 0.31 g (19%) of a white solid as the title compound. 1H NMR (400 MHz, DMSO-D6) δ 1.25-1.44 (m, 4 H), 1.46 (s, 9 H), 2.05-2.24 (m, 1 H), 3.15 (m, 2 H), 3.77 (m, 2 H), 4.28 (d, J=7.03 Hz, 2 H), 5.38 (s, 2 H), 5.78 (d, J=2.93 Hz, 1 H), 7.63 (dd, J=8.79, 1.76 Hz, 1 H), 7.82 (d, J=8.59 Hz, 1 H), 7.97 (d, J=1.76 Hz, 1 H), 8.00 (d, J=2.93 Hz, 1 H); MS (ESI) (M+H)+=417.8; Anal. Calcd for C20H27N5O3S+1.30 TFA+0.10 EtOAc (575.78): C, 48.19; H, 5.09; N, 12.16. Found: C, 48.12; H, 5.02; N, 12.29.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-6a7ca8aecfd243d88f06ef50cec7c448
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…