Ethyl isocyanate → 4-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate

HRID 347458Notes

Reaction equation

HRID 347458 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:15])[C:12]([OH:14])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.CCN(C(C)C)C(C)C.[CH2:32]([N:34]=[C:35]=[O:36])[CH3:33]>C(Cl)Cl>[CH2:32]([NH:34][C:35](=[O:36])[O:14][C:12]1[C:11]([CH3:15])=[C:10]2[N:9]([CH:13]=1)[N:8]=[CH:7][N:6]=[C:5]2[O:4][C:3]1[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:2]=1[F:1])[CH3:33]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 210816464-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-ol2×

Product 1

HCID 210816474-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamateYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-ol (25 mg, 0.082 mmol, Compound F of Example 1), DIEA (0.017 mL, 0.1 mmol) in CH2Cl2 (5 mL) was added ethyl isocyanate (0.078 mL, 0.1 mL) and stirred at room temperature for 2 h. The reaction was quenched with water (5 mL). The organic layer was separated, dried and concentrated in vacuo. The mixture was purified by flash chromatography (1–5% Methanol/CH2Cl2) to give the title compound (12.5 mg, 32%) as a white solid.

Workup

  1. customThe reaction was quenched with water (5 mL)
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe mixture was purified by flash chromatography (1–5% Methanol/CH2Cl2)

Sources & evidence

ORD record
ord-ef706005b7ee43d0a0a0a1fb25593011
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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