Methanol → 3-[(methylamino)methyl]-1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-ol

HRID 16012Notes

Reaction equation

[O:1]1[C:3]2([CH2:7][CH2:6][N:5]([C:8]3[N:13]=[C:12]4[N:14]([CH2:17][C:18]5[CH:19]=[C:20]6[C:25](=[CH:26][CH:27]=5)[N:24]=[CH:23][CH:22]=[CH:21]6)[N:15]=[N:16][C:11]4=[N:10][CH:9]=3)[CH2:4]2)[CH2:2]1.CO.[CH3:30][NH2:31].[I-].[K+]>CS(C)=O>[CH3:30][NH:31][CH2:2][C:3]1([OH:1])[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)[N:15]=[N:16][C:11]3=[N:10][CH:9]=2)[CH2:4]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-{[6-(1-oxa-5-azaspiro[2.4]hept-5-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl]methyl}quinoline (130 mg, 0.36 mmol) in 2:1 MeOH:DMSO (3 ml) were added methylamine (24.7 mg, 0.80 mmol) and potassium iodide (300.4 mg, 1.81 mmol) at R.T. After heating at 80° C. for 3.5 h, the reaction mixture was cooled to R.T. and concentrated under reduced pressure. The resulting residue was purified via flash column chromatography eluted with 0-5% 7N N3 in MeOH: CH2Cl2 to give the desired product (35 mg, 25%).

Workup

temperaturethe reaction mixture was cooled to R.T.
concentrationconcentrated under reduced pressure
customThe resulting residue was purified via flash column chromatography
washeluted with 0-5% 7N

Sources & evidence

ORD record: ord-ae32f22fcd2c41e1850652436b808744
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732604B2

Reaction notes

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