Triethylamine → HCID 58204936, compound

HRID 2044733Notes

Reaction equation

HRID 2044733 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH2:23][OH:24])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].ClC(Cl)(Cl)[C:27]([N:29]=C=O)=[O:28].C(N(CC)CC)C>C1COCC1.O>[C:27](=[O:28])([O:24][CH2:23][C:21]1[CH:20]=[CH:19][C:16]2[C:17]3[N:11]([CH:10]=[C:9]([C:8]4[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][N:7]=4)[N:18]=3)[CH2:12][CH2:13][O:14][C:15]=2[CH:22]=1)[NH2:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 67050768HCID 67050768, compound

Product 1

HCID 58204936HCID 58204936, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-methanol (0.10 g, 0.31 mmol) in THF (1 mL) cooled to −78° C. was added trichloroacetyl isocyanate (40 μL, 0.47 mmol). The resultant mixture was allowed to warm to 0° C. before triethylamine (0.17 mL) and water (0.3 mL) were added and the mixture stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 10% methanol in DCM) to give 547 (0.095 g, 83%). LCMS: RT=3.34 min, [M+H]+=369. 1H-NMR 400 MHz (DMSO-d6): δ 8.39 (1H, d, J=8.24 Hz), 7.92-7.92 (2H, m), 7.11 (1H, dd, J=8.30, 1.71 Hz), 7.02 (1H, d, J=1.63 Hz), 5.88-5.87 (1H, m), 4.99 (2H, s), 4.55-4.49 (4H, m), 3.29 (2H, s), 1.48 (6H, d, J=6.60 Hz)

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b1bc06d49f24148bf97defb6ce11ee3
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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