Pyrrolidine → HCID 178489386, compound

HRID 272033Notes

Reaction equation

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

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 178497684HCID 178497684, compound

Product 1

HCID 178489386HCID 178489386, compoundYield 67%

Conditions

Temperature: 90 °C

Procedure

3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid methyl ester (30 mg, 83 μmol) was dissolved in pyrrolidine (0.35 ml, 4.15 mmol) and the mixture was stirred at 90° C. for 16 h. The mixture was then concentrated and the crude product purified by flash silica gel chromatography using a gradient of 10% v/v of methanol in ethyl acetate to afford {3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-pyrrolidin-1-yl-methanone as a yellow solid (22 mg, 55 μmol, 67% yield). 1H-NMR (500 MHz, d6-MeOH) δ8.82 (d, 1H), 8.39 (d, 1H), 7.83 (t, 1H), 7.79 (td, 1H), 7.66 (dd, 1H), 7.55-7.59 (m, 2H), 7.48 (ddd, 1H), 7.20 (d, 1H), 7.11 (dt, 1H), 3.88 (s, 3H), 3.63 (t, 2H), 3.52 (t, 2H), 2.02 (m, 2H), 1.92 (m, 2H). MS: m/z 399 [MH+].

Workup

concentrationThe mixture was then concentrated
customthe crude product purified by flash silica gel chromatography

Sources & evidence

ORD record: ord-d73507b57f35485086d4de234c7fb935
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452993B2

Reaction notes

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