Ethyl orthoformate → HCID 86726636, compound

HRID 1506215Notes

Reaction equation

[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]3[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:28](OCC)(OCC)[O:29]CC>>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH:16][CH:28]=[O:29])=[O:15])=[CH:12][N:11]=[C:10]3[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 71258449HCID 71258449, compound

Product 1

HCID 86726636HCID 86726636, compoundYield 27%

Procedure

4-(Cyclohexylamino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (45 mg, 0.12 mmol) in triethyl orthoformate (2 mL) was stirred at 120° C. for one day. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→0/1 (v/v)) to give the title compound as a pale yellow amorphous (12.4 mg, yield 27%).

Workup

concentrationconcentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→0/1 (v/v))

Sources & evidence

ORD record: ord-8fe5eb55c18a40ada8e691177651a5c7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216999B2

Reaction notes

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