Dichloromethane → 5-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)-1-methyl 1H-pyrazole-4-carboxamide

HRID 1773718Notes

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[N:32]([CH3:33])[N:31]=[CH:30][C:29]=1[C:34]#[N:35].C(Cl)Cl.C1CCN2C(=NCCC2)CC1.CS(C)=[O:52].O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:28]3[N:32]([CH3:33])[N:31]=[CH:30][C:29]=3[C:34]([NH2:35])=[O:52])[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

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vial containing 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 (100 mg, 0.28 mmol, 1 equiv.) was added 5-bromo-1-methyl-1H-pyrazole-4-carbonitrile (130 mg, 0.30 mmol, 2.5 equiv.), Pd(dppf)Cl2.CH2Cl2 (23 mg, 0.03 mmol, 0.1 equiv.) and DBU (253 μL, 1.69 mmol, 6 equiv.) and dissolved in DMSO-H2O (4 mL, 0.2 M, 2/1, v/v). The mixture was heated to 120° C. for 30 min in microwave. The reaction was concentrated in vacuo and purification was then carried out by reverse phase HPLC.

Workup

concentrationThe reaction was concentrated in vacuo and purification

Sources & evidence

ORD record: ord-3060c97c352f4e109e4f5dfcb7340b10
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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