Potassium Phosphate, Tribasic → 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

HRID 1852902Notes

Reaction equation

HRID 1852902 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:26][CH2:25]4)=[CH:20][CH:19]=3)[C:11]3=[N:12][C:13](Cl)=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:36]([O:39][C:40]([CH3:60])([CH3:59])[C:41](=[O:58])[NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45](B2OC(C)(C)C(C)(C)O2)[CH:44]=1)(=[O:38])[CH3:37].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[C:36]([O:39][C:40]([CH3:60])([CH3:59])[C:41]([NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([C:13]2[N:12]=[C:11]3[N:17]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([NH:28][C:29]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:35])[CH2:27][CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[C:8]([C:7]4[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=4)=[N:9][C:10]3=[CH:15][CH:14]=2)[CH:44]=1)=[O:58])(=[O:38])[CH3:37]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 711386561,1-Dimethyl-2-oxo-2-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amino}ethyl acetateHCID 86675348tert-butyl (1-(4-(2-(2-aminopyridin-3-yl)-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 711384412-({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 acetateYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate (50 mg) and 1,1-dimethyl-2-oxo-2-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amino}ethyl acetate (71 mg) and potassium phosphate (65 mg) and PdCl2(dppf)CH2Cl2 (8 mg) in dioxane (2 mL) and H2O (0.2 mL) was degassed for 5 minutes and then heated to 80° C. for 18 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (2 times: 0-10% methanol in chloroform then 0-10% methanol in ethyl acetate) gave the product (44 mg, 64%).

Workup

  1. customwas degassed for 5 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customPurification by column chromatography (2 times

Sources & evidence

ORD record
ord-3649428b83de4fe6a6c39a4d9d82df7c
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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