Ethyl formate → HCID 58382093, compound

HRID 1628014Notes

Reaction equation

[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([CH2:12][NH2:13])[N:10]=2)[N:5]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:4]=1[C:22]1[CH:27]=[CH:26][C:25]([C:28]2([CH3:33])[O:32][CH2:31][CH2:30][O:29]2)=[CH:24][CH:23]=1)[CH3:2].[CH:34](OCC)=[O:35]>>[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([CH2:12][NH:13][CH:34]=[O:35])[N:10]=2)[N:5]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:4]=1[C:22]1[CH:23]=[CH:24][C:25]([C:28]2([CH3:33])[O:32][CH2:31][CH2:30][O:29]2)=[CH:26][CH:27]=1)[CH3:2]

Participants

Reactant 2

HCID 8025Ethyl formate

HCID 58382194HCID 58382194, compound

Product 1

HCID 58382093HCID 58382093, compoundYield 100.1%

Procedure

(7-Ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.250 g, 0.533 mmol, prepared using D from Preparation #5 with (E)-styrylboronic acid, E, F, G and I) in ethyl formate (3.30 mL, 40.5 mmol) was heated to about 65° C. for about 2 h. The mixture was cooled to rt then the solvent was re removed under reduced pressure to give N-((7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)formamide (0.265 g, 100%): LC/MS (Table 2, Method b) Rt=2.71 min; MS m/z 497 (M+H)+.

Workup

customthe solvent was re removed under reduced pressure

Sources & evidence

ORD record: ord-fc940ac2f68c4de18eb61874759d67a9
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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