Ethyl isocyanate → HCID 54671411, compound

HRID 1522644Notes

Reaction equation

HRID 1522644 reaction equation
[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]4[CH:22]=[N:23][NH:24][C:17]=34)[C:12]([CH3:25])=[CH:11][N:10]=2)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[N:26]([CH2:29][CH3:30])=[C:27]=[O:28]>N1C=CC=CC=1.C(#N)C>[CH2:29]([NH:26][C:27]([N:24]1[C:17]2[C:18](=[N:19][CH:20]=[CH:21][C:16]=2[NH:15][C:13]2[C:12]([CH3:25])=[CH:11][N:10]=[C:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[C:5]([CH3:8])[N:4]=3)[CH:14]=2)[CH:22]=[N:23]1)=[O:28])[CH3:30]

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 67469580HCID 67469580, compound

Product 1

HCID 54671411HCID 54671411, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

N-(3′-Fluoro-5,6′-dimethyl-2,2′-bipyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine (81 mg, 0.242 mmol) was combined with acetonitrile (2.4 mL) and isocyanatoethane (23.78 μl, 0.303 mmol) along with 1 drop of pyridine. The mixture was heated at 75° C. The reaction was then cooled to give a solid which was collected by filtration, rinsed with acetonitrile to give the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.35 (3H, t, J=7.20 Hz) 2.47 (3H, s) 2.64 (3H, s) 3.51-3.63 (2H, m) 7.17-7.23 (1H, m) 7.33 (1H, d, J=4.55 Hz) 7.43 (1H, dd, J=10.48, 8.46 Hz) 7.51-7.59 (1H, m) 8.08 (1H, br. s.) 8.27 (1H, s) 8.41 (1H, d, J=5.31 Hz) 8.65 (1H, br. s.) 11.00 (1H, br. s.). MS [M+H] found 406.4.

Workup

  1. temperatureThe reaction was then cooled
  2. customto give a solid which
  3. filtrationwas collected by filtration
  4. washrinsed with acetonitrile

Sources & evidence

ORD record
ord-671ff2bbe02a4d8685c687da3abf6d2e
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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