Toluene → HCID 57385852, compound

HRID 1503361Notes

Reaction equation

[CH:1]1([NH:4][C:5](=[O:25])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[CH:17]=[C:18]([Br:22])[N:19]=[C:20](Br)[C:15]4=[N:14][C:13]=3[CH2:23][OH:24])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[CH3:26][CH:27]([CH3:30])[CH2:28][NH2:29].C1(C)C=CC=CC=1>CN(C)C=O>[Br:22][C:18]1[N:19]=[C:20]([NH:29][CH2:28][CH:27]([CH3:30])[CH3:26])[C:15]2[N:16]([C:12]([C:9]3[CH:8]=[CH:7][C:6]([C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:25])=[CH:11][CH:10]=3)=[C:13]([CH2:23][OH:24])[N:14]=2)[CH:17]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 50 mg (107 μmol) N-cyclopropyl-4-[6,8-dibromo-2-(hydroxymethyl)imidazo[1,2-a]pyrazin-3-yl]benzamide in 0.71 mL N,N-dimethylformamide were added 32 μL 2-methylpropan-1-amine and the mixture was stirred at 23° C. for 3 hours. Toluene was added and the solvents removed. The residue was purified by chromatography to give 40.7 mg (83%) of the title compound. 1H-NMR (300 MHz d6-DMSO): δ=8.52 (1H, d), 8.12 (1H, t), 7.95 (2H, d), 7.68 (2H, d), 7.50 (1H, s), 5.18 (1H, t), 4.46 (2H, d), 3.23 (2H, m), 2.85 (1H, m), 2.00 (1H, m), 0.87 (6H, m), 0.68 (2H, m), 0.55 (2H, m) ppm. UPLC-MS: RT=1.18 min; m/z 459.4 [MH+]; required MW=458.4.

Workup

customthe solvents removed
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-78ed0886908347bfbc6ec8da14be2330
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212184B2

Reaction notes

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