Triethylamine → HCID 136186307, compound

HRID 907957Notes

Reaction equation

HRID 907957 reaction equation
[C:1]1([CH:7]2[C:12]3=[N:13][NH:14][C:15](=[O:20])[C:16]4[CH:17]=[CH:18][CH:19]=[C:10]([C:11]=43)[NH:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCOCC1.CCN(CC)CC>C1COCC1>[C:1]1([CH:7]2[C:12]3=[N:13][NH:14][C:15](=[O:20])[C:16]4[CH:17]=[CH:18][CH:19]=[C:10]([C:11]=43)[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 136374695HCID 136374695, compound

Product 1

HCID 136186307HCID 136186307, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 9-phenyl-2H-pyrido[4,3,2-de]phthalazine-3,8(7H,9H)-dione (80 mg, 2.2 mmol), BH3 (0.7 mL, 1 mol/L in THF), dioxane (4 mL) in sealed tube was stirred for 2 h at 95° C. under nitrogen atmosphere. Then the mixture was treated with MeOH˜HCl (g) (0.2 mL), stirred for 20 min at 95° C. Then the mixture was cooled and adjusted to pH=8 with Et3N. The solvent was removed under vacuum and the crude was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 1:1) to obtain the title compound as a yellow solid (l 8.3 mg, yield 24%). LC-MS (ESI) m/z: 264 (M+1)+. 1H-NMR (400 MHz, CD3OD) δ (ppm): 3.60-3.64 (m, 1H), 3.68-3.72 (m, 1H), 4.21 (t, J=5.2 Hz, 1H), 7.09-7.11 (d, J=8 Hz, 1H), 7.16-7.29 (m, 5H), 7.53-7.61 (m, 2H).

Workup

  1. stirringstirred for 20 min at 95° C
  2. temperatureThen the mixture was cooled
  3. customThe solvent was removed under vacuum
  4. customthe crude was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 1:1)

Sources & evidence

ORD record
ord-54c1fb9dccd340c7aad514fb6db6eadf
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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