Ethyl isocyanate → HCID 54670783, compound

HRID 1522623Notes

Reaction equation

HRID 1522623 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)[CH:12]=[CH:11][N:10]=1.[N:25]([CH2:28][CH3:29])=[C:26]=[O:27]>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:26]([NH:25][CH2:28][CH3:29])=[O:27])[C:17]=23)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 54670693HCID 54670693, compound

Product 1

HCID 54670783HCID 54670783, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

N-(2-(2,5-Difluorophenyl)pyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine (50.7 mg, 0.157 mmol) was suspended in acetonitrile (16 mL), isocyanatoethane (12.32 μl, 0.157 mmol) was added and the reaction was stirred at 70° C. for 2 hours, cooled to give a solid. The solid was collected by filtration, rinsed with acetonitrile (3×15 mL) and ether (3×5 mL) and dried under high vacuum to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (3H, t, J=7.20 Hz) 3.36-3.46 (2H, m) 7.31-7.47 (3H, m) 7.52 (1H, d, J=5.31 Hz) 7.67 (1H, s) 7.77 (1H, ddd, J=9.47, 6.06, 3.16 Hz) 8.45 (1H, d, J=5.31 Hz) 8.58-8.63 (2H, m) 9.10 (1H, s) 11.43 (1H, s). MS [M+H] found 395.4.

Workup

  1. temperaturecooled
  2. customto give a solid
  3. filtrationThe solid was collected by filtration
  4. washrinsed with acetonitrile (3×15 mL) and ether (3×5 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-2efadacad1cc4bbda08108d8bdeee3cc
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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