Ethyl isocyanate → HCID 54670782, compound

HRID 1522622Notes

Reaction equation

HRID 1522622 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N: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])=[C:11]([CH3:26])[N:10]=1.[N:27]([CH2:30][CH3:31])=[C:28]=[O:29]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[N:23][N:24]([C:28]([NH:27][CH2:30][CH3:31])=[O:29])[C:17]=23)[C:12]([CH3:25])=[C:11]([CH3:26])[N:10]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 67470725HCID 67470725, compound

Product 1

HCID 54670782HCID 54670782, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

N-(2-(2,5-Difluorophenyl)-5,6-dimethylpyrimidin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine (0.081 g, 0.230 mmol) was suspended in acetonitrile (2.3 mL), isocyanatoethane (0.018 mL, 0.230 mmol) was added and the mixture was stirred at 70° C. for 2 hours. The reaction was filtered and purified on silica column chromatography using a step gradient of 0 to 5% MeOH in DCM to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20-1.27 (3H, m) 2.40 (3H, s) 2.54 (3H, s) 3.37-3.48 (2H, m) 7.35-7.47 (2H, m) 7.76-7.87 (1H, m) 8.51 (1H, d, J=5.56 Hz) 8.64 (1H, s) 8.97 (1H, d, J=5.31 Hz) 9.11-9.19 (1H, m) 11.94 (1H, s). MS [M+H] found 424.4.

Workup

  1. filtrationThe reaction was filtered
  2. custompurified on silica column chromatography

Sources & evidence

ORD record
ord-54ec82e283a44fc8a5acb2e9b00da4d3
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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