Carbon Dioxide → HCID 59232026, compound

HRID 1099291Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH2:11][CH2:12][OH:13])[N:6]2[N:5]=[CH:4][N:3]=1.CC(O)C.C(=O)=O.[Br:21]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([Br:21])[CH:9]=[C:10]([CH2:11][CH2:12][OH:13])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)ethanol (777 mg, 4.3 mmol) in DMF (22 mL) at −20° C. (IPA and dry ice) was added 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione (359 mg, 1.72 mmol) ) was added in 4 portions within 20 min. The reaction was stirred at −20° C. for 30 min. Analytical HPLC indicated 22% starting material remanded, additional B (90 mg, 0.30 mmol) was added and stirred for 20 min. The reaction was quenched with satd. Na2SO3 and warmed up to rt. The crude was extracted w/EtOAc 5×. The organic was washed with 5% aq K2CO3 and brine. Dried over Na2SO4 and concentrated. The crude was purified by MPLC with 0-7% MeOH/CH2Cl2 to give 814 mg of desired product (yield, 72.6%). MS [M+H]+=257.3; LCMS RT=1.14 min.

Workup

additionwas added in 4 portions within 20 min
additionadditional B (90 mg, 0.30 mmol) was added
stirringstirred for 20 min
customThe reaction was quenched with satd
temperatureNa2SO3 and warmed up to rt
extractionThe crude was extracted w/EtOAc 5×
washThe organic was washed with 5% aq K2CO3 and brine
dry with materialDried over Na2SO4
concentrationconcentrated
customThe crude was purified by MPLC with 0-7% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-25076a287c4742a6ba7bf06ad10af923
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143393B2

Reaction notes

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