Isopropyl isocyanate → 7-(2-(2,5-difluorophenyl)-5-methylpyridin-4-ylamino)-N-isopropyl-1H-pyrazolo[4,3-b]pyridine-1-carboxamide

HRID 1522642Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[N:23][NH:24][C:17]=23)[C:12]([CH3:25])=[CH:11][N:10]=1.[N:26]([CH:29]([CH3:31])[CH3:30])=[C:27]=[O:28]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[N:23][N:24]([C:27]([NH:26][CH:29]([CH3:31])[CH3:30])=[O:28])[C:17]=23)[C:12]([CH3:25])=[CH:11][N:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-(2-(2,5-Difluorophenyl)-5-methylpyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine (100 mg, 0.296 mmol) was suspended in acetonitrile (3 mL). 2-Isocyanatopropane (29.1 μl, 0.296 mmol) was added and the reaction was stirred at 70° C. for 2 hours. The mixture was then cooled to give a solid which was collected by filtration to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (6H, d, J=6.57 Hz) 2.38 (3H, s) 4.05-4.19 (1H, m) 7.26-7.45 (3H, m) 7.76 (1H, ddd, J=9.41, 6.13, 3.16 Hz) 7.93 (1H, s) 8.35-8.44 (1H, m) 8.54 (1H, s) 8.60 (1H, s) 8.82 (1H, d, J=8.34 Hz) 11.01 (1H, s). MS [M+H] found 423.5.

Workup

temperatureThe mixture was then cooled
customto give a solid which
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-c00234e9c8ef45a5adf017d8842fe254
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073918B2

Reaction notes

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