1,2-Dimethoxyethane → 4-(5-amino-2-cyclopropylpyridin-3-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773696Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9](B3OC(C)(C)C(C)(C)O3)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:26])[O:4][N:3]=1.Br[C:28]1[CH:29]=[C:30]([NH2:37])[CH:31]=[N:32][C:33]=1[CH:34]1[CH2:36][CH2:35]1.COCCOC.C([O-])([O-])=O.[Cs+].[Cs+]>O>[NH2:37][C:30]1[CH:29]=[C:28]([C:9]2[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=[C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:26])[CH:8]=2)[C:33]([CH:34]2[CH2:36][CH2:35]2)=[N:32][CH:31]=1

Participants

Conditions

Temperature: 130 °C

Procedure

6-(3,5-dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (150 mg, 0.42 mmol) and 5-bromo-6-cyclopropylpyridin-3-amine (180 mg, 0.84 mmol) were added to a solvent mixture of 1,2-dimethoxyethane (2 mL) and water (1 mL). To the mixture were added PEPPSI-Ipr (29 mg, 0.03 mmol) and Cs2CO3 (413 mg, 1 mmol). The reaction mixture was heated at 130° C. in microwave reactor for 30 mins. The reaction mixture was then filtered and organic solvent was evaporated and the residue was purified with Prep HPLC (0-100% CH3CN/H2O) to afford 129 mg of 4-(5-amino-2-cyclopropylpyridin-3-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one.

Workup

filtrationThe reaction mixture was then filtered
customorganic solvent was evaporated
customthe residue was purified with Prep HPLC (0-100% CH3CN/H2O)

Sources & evidence

ORD record: ord-c70ffc66f6a941628232e056265a274b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

Loading…