1,2-Dichloroethane → HCID 58180923, compound

HRID 1772823Notes

Reaction equation

[C:1]([CH2:3][CH:4]([CH:27]1[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]1)[N:5]1[CH:9]=[C:8]([C:10]2[C:11]3[CH:18]=[CH:17][N:16](COCC[Si](C)(C)C)[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[N:6]1)#[N:2].ClCCCl.FC(F)(F)C(O)=O.CO.C(N)CN>>[NH:30]1[CH2:29][CH2:28][CH:27]([CH:4]([N:5]2[CH:9]=[C:8]([C:10]3[C:11]4[CH:18]=[CH:17][NH:16][C:12]=4[N:13]=[CH:14][N:15]=3)[CH:7]=[N:6]2)[CH2:3][C:1]#[N:2])[CH2:32][CH2:31]1

Participants

Reactant 5

HCID 111,2-Dichloroethane

HCID 887Methanol

HCID 3301Ethylenediamine

HCID 6422Trifluoroacetic acid

HCID 58180890HCID 58180890, compound

Product 1

HCID 58180923HCID 58180923, compoundYield 82.1%

Procedure

A solution of tert-butyl 4-{2-cyano-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}piperidine-1-carboxylate (2.0 g, 0.0036 mol) in 1,2-dichloroethane (20 mL, 0.2 mol) and trifluoroacetic acid (20 mL, 0.2 mol) was stirred for 1.1 hour, then the solvent was removed by rotary evaporation to give a colorless oil. The thick oil was dissolved in methanol (15 mL, 0.37 mol) and ethylenediamine (1.0 mL, 0.015 mol) was added. After 1.1 hours, the reaction was purified by preparative-LCMS (pH 10) to give 0.95 g white solid (82% yield). LCMS (M+1): 322.

Workup

customthe solvent was removed by rotary evaporation
customto give a colorless oil
customthe reaction was purified by preparative-LCMS (pH 10)

Sources & evidence

ORD record: ord-db08745c248243a2bb12a69e3889eb1a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249145B2

Reaction notes

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