Methanol → HCID 71053059, compound

HRID 870004Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]([NH:15][C:16]4[N:21]=[C:20](C5C=CN=C(OC)C=5)[C:19]([CH3:30])=[CH:18][CH:17]=4)=[O:14])[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Si](I)(C)(C)C.[CH3:36][OH:37]>C(C#N)(C)=O>[O:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([CH3:30])=[C:20]([C:10]5[CH:7]=[CH:6][C:36](=[O:37])[NH:15][CH:13]=5)[N:21]=4)=[O:14])[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a slurry of 1-(2,3-dihydrobenzofuran-6-yl)-N-(2′-methoxy-3-methyl-2,4′-bipyridin-6-yl)cyclopropanecarboxamide (25 mg, 0.062 mmol) in AcCN (1.5 mL) was added TMS-I (35.45 μL, 0.24 mmol) and stirred at 55° C. for 7 h. The reaction was diluted with methanol (1.0 mL) and stirred at room temperature for 2 h. The resulting mixture was concentrated under vacuum, and taken into ethyl acetate (10 mL. The organic solution washed with sodium bisulphate (2×2 ml) water (2×3 mL), dried over sodium sulphate and concentrated under vacuum. The solid was stirred with methanol (1.0 mL) at 40° C. for 10 min and collected by filtration, washed with methanol (1.0 mL) and dried under vacuum to yield 18.0 mg (74%) of the desired product. ESI-MS m/z calc. 387.4. found 388.2 (M+1)+. Retention time 1.32 minutes.

Workup

stirringstirred at room temperature for 2 h
concentrationThe resulting mixture was concentrated under vacuum
washThe organic solution washed with sodium bisulphate (2×2 ml) water (2×3 mL)
dry with materialdried over sodium sulphate
concentrationconcentrated under vacuum
stirringThe solid was stirred with methanol (1.0 mL) at 40° C. for 10 min
filtrationcollected by filtration
washwashed with methanol (1.0 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-6a41bbf4c5554b7f818721557e3c2b79
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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