Carbonate Ion → tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[(2-hydroxy-2-methylpropanoyl)amino]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate

HRID 1914009Notes

Reaction equation

C([O:4][C:5]([CH3:50])([CH3:49])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:20]=[C:19]3[N:21]([C:31]4[CH:36]=[CH:35][C:34]([C:37]5([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40][CH2:39][CH2:38]5)=[CH:33][CH:32]=4)[C:22]([C:24]4[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][CH:29]=4)=[N:23][C:18]3=[CH:17][CH:16]=2)[CH:10]=1)=[O:7])(=O)C.C(=O)([O-])[O-]>CO>[NH2:30][C:25]1[C:24]([C:22]2[N:21]([C:31]3[CH:32]=[CH:33][C:34]([C:37]4([NH:41][C:42](=[O:43])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:38][CH2:39][CH2:40]4)=[CH:35][CH:36]=3)[C:19]3=[N:20][C:15]([C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6](=[O:7])[C:5]([OH:4])([CH3:50])[CH3:49])[CH:10]=4)=[CH:16][CH:17]=[C:18]3[N:23]=2)=[CH:29][CH:28]=[CH:27][N:26]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-({3-[2-(2-aminopyridin-3-yl)-3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3H-imidazo[4,5-b]pyridin-5-yl]phenyl}amino)-1,1-dimethyl-2-oxoethyl acetate (24 mg) in methanol (6 mL) was added MP-carbonate (Argonaout technologies 2.91 mmol/g, 200 mg) at room temperature. After being stirred at 40° C. for 4 h, the reaction mixture was filtered and concentrated under reduced pressure. Purification by column chromatography (0-10% methanol in chloroform) gave the product (20 mg, 91%).

Workup

filtrationthe reaction mixture was filtered
concentrationconcentrated under reduced pressure
customPurification by column chromatography (0-10% methanol in chloroform)

Sources & evidence

ORD record: ord-61a92c82330d4e9bab98ed4adb43aa7d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609688B2

Reaction notes

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