2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 58365132, compound

HRID 60311Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:15]3[C:14]4[CH:16]=[C:17]([C:20]#[N:21])[N:18]=[CH:19][C:13]=4[N:12]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:11]=3[N:10]=[CH:9][CH:8]=2)[CH2:3]1.FC(F)(F)S(O[CH2:36][C:37]([F:40])([F:39])[F:38])(=O)=O.C(N(CC)C(C)C)(C)C>C(Cl)Cl.O>[F:38][C:37]([F:40])([F:39])[CH2:36][NH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:15]3[C:14]4[CH:16]=[C:17]([C:20]#[N:21])[N:18]=[CH:19][C:13]=4[N:12]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:11]=3[N:10]=[CH:9][CH:8]=2)[CH2:3]1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of (S)-4-(3-aminopyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (131 mg, 0.32 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (490 mg, 2.1 mmol), and N,N-diisopropylethylamine (365 uL, 2.1 mmol) in methylene chloride (15 mL) was heated at 40° C. for 4 hours. The cooled reaction mixture was diluted with water (20 mL) and methylene chloride (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 4 g, ISCO, 0-20% methanol in methylene chloride) to afford the title compound as an oil, which was used in the next step without any further purification (156 mg, 100%).

Workup

customThe cooled reaction mixture
customThe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by flash chromatography (silica, 4 g, ISCO, 0-20% methanol in methylene chloride)

Sources & evidence

ORD record: ord-78ef34cc294541cda2126ce79da60cdc
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440976B2

Reaction notes

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