Ethyl isocyanate → HCID 136414381, compound

HRID 1034975Notes

Reaction equation

HRID 1034975 reaction equation
[CH:1]1([C:5]2[C:6]([C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=3)=[C:7]([NH2:17])[N:8]([CH2:10][C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N=[C:27]=[O:28])C>N1C=CC=CC=1>[CH:1]1([C:5]2[C:6]3[C:18]4[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=4[C:27](=[O:28])[NH:17][C:7]=3[N:8]([CH2:10][C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 69180200HCID 69180200, compound

Product 1

HCID 136414381HCID 136414381, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Example 85C (4 g, 18 mmol) in anhydrous pyridine (50 mL) was added ethyl isocyanate (3 mL) under nitrogen. The solution was heated at 50° C. for 6 h and under reflux overnight. The volatile were removed and the residual solid was purified by flash chromatography to give Example 85D. Yield: 4.2 g (70%). MS (DCI): m/z 335 (M+H)+, 1H NMR (300 MHz, CDCl3) δ 1.58 (s, 1H), 1.72-1.86 (m, 5H), 1.87-2.17 (m, 2H), 2.27-2.61 (m, 6H), 2.84 (s, 2H), 3.62-3.90 (m, 1H), 7.20 (dd, J=7.80, 4.75 Hz, 1H), 7.78 (d, J=7.80 Hz, 1H), 8.48 (d, J=3.05 Hz, 1H), 8.77 (s, 1H).

Workup

  1. temperatureunder reflux overnight
  2. customThe volatile were removed
  3. customthe residual solid was purified by flash chromatography
  4. customto give Example 85D

Sources & evidence

ORD record
ord-3f0151f2e16e41bd8ef96f826452b926
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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