HCID 57863422, compound → HCID 135979853, compound

HRID 1446743Notes

Reaction equation

[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]4[CH:26]=[CH:27][C:28]([C:30]5[CH:31]=[N:32][C:33]([O:36]C)=[CH:34][CH:35]=5)=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:17][CH:16]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>Br>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]4[CH:26]=[CH:27][C:28]([C:30]5[CH:35]=[CH:34][C:33](=[O:36])[NH:32][CH:31]=5)=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:19][CH:20]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve 1-(5-tert-butyl-isoxazol-3-yl)-3-{4-[7-(6-methoxy-pyridin-3-yl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-urea (0.408 g, 0.82 mmol, 1.0 eq.) in HBr (˜48%, 4 mL) and stir at 80° C. overnight under nitrogen. Evaporate the reaction mixture under vacuum and purify in four steps: 1) flash SCX, 2) reverse phase HPLC The mixture is purified via reversed phase C18 column HPLC employing a gradient of 5 to 65% acetonitrile vs 0.03% aqueous HCl, 3) flash SCX, and 4) silica gel chromatography using a 0-10% MeOH/DC gradient to give the title compound 0.156 g as a white solid: MS(ES), m/z 483 (M+1).

Workup

customEvaporate the reaction mixture under vacuum
custompurify in four steps
customis purified via reversed phase C18 column HPLC

Sources & evidence

ORD record: ord-19774e61609e47c18d04a23882c11c00
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666879B2

Reaction notes

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