Ethyl isocyanate → HCID 67470524, compound

HRID 1522630Notes

Reaction equation

HRID 1522630 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])=[CH:11][N:10]=1.[N:26]([CH2:29][CH3:30])=[C:27]=[O:28]>C(#N)C.N1C=CC=CC=1>[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:27]([NH:26][CH2:29][CH3:30])=[O:28])[C:17]=23)[C:12]([CH3:25])=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 54670786HCID 54670786, compound

Product 1

HCID 67470524HCID 67470524, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To N-(2-(2,5-Difluorophenyl)-5-methylpyrimidin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine (108 mg, 0.319 mmol) suspended in acetonitrile (3.2 mL) was added isocyanatoethane (125.3 μl, 1.60 mmol), 15 drops of pyridine and the mixture was heated at 70° C. overnight. The reaction was cooled to give a solid which was collected by filtration, rinsed with a acetonitrile, and dried under high vacuum to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (3H, t, J=7.20 Hz) 2.43 (3H, s) 3.37-3.48 (2H, m) 7.36-7.51 (2H, m) 7.85 (1H, ddd, J=9.22, 5.94, 3.03 Hz) 8.47-8.57 (1H, m) 8.65 (1H, s) 9.06 (1H, d, J=5.30 Hz) 9.13 (1H, t, J=5.94 Hz) 12.07 (1H, s). MS [M+H] found 410.4.

Workup

  1. temperatureThe reaction was cooled
  2. customto give a solid which
  3. filtrationwas collected by filtration
  4. washrinsed with a acetonitrile
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-46cec644894140c9b2d29f15e5d7d440
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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