2-Methylbenzenesulfonic acid hydrate → HCID 178468783, compound

HRID 1433208Notes

Reaction equation

C([Si](C)(C)[O:6][C:7]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[CH:37]=[CH:36][C:20]3[NH:21][C:22]([CH2:24][O:25][C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)=[N:23][C:19]=3[CH:18]=2)[CH:9]([CH3:10])[O:8]1)(C)(C)C.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1COCC1>[OH:8][CH:9]([CH3:10])[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:37]=[CH:36][C:20]2[NH:21][C:22]([CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:28][CH:27]=3)=[N:23][C:19]=2[CH:18]=1)=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-{2-[2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oxiranyl]-phenyl}-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole (0.040 g, 0.0721 mmol) and toluenesulfonic acid monohydrate (0.016 g, 0.0865 mmol) in THF (2 mL) was heated to 80° C. for 4 hours. The reaction mixture was then concentrated, and the residue was purified by chromatography (silica, hexanes: EtOAc, 1:2) to afford the title compound as a brown oil (0.028 g, 89%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.66-7.56 (m, 4H), 7.53-7.45 (m, 4H), 7.26-7.22 (m, 3H), 5.43 (s, 2H), 4.12-4.03 (m, 1H), 1.03 (d, 3H, J=7.2 Hz). Mass Spectrum (LCMS, ESI pos.) Calcd. For C26H23F3N3O3: 482.4 (M+MeCN+H), Found 482.3.

Workup

concentrationThe reaction mixture was then concentrated
customthe residue was purified by chromatography (silica, hexanes: EtOAc, 1:2)

Sources & evidence

ORD record: ord-1bf3c06808ec48adbf9c460a926a8f19
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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