Triethylamine → HCID 89107007, compound

HRID 1853292Notes

Reaction equation

HRID 1853292 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]#[C:18][CH2:19][CH2:20][OH:21])=[CH:14][CH:15]=2)[O:10][C:9]([C:22]2[N:23]=[CH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41].[Na]>ClCCl>[C:1]([O:5]/[N:6]=[C:7]1\[CH:8]=[C:9]([C:22]2[N:23]=[CH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:10][C:11]2[C:16]\1=[CH:15][CH:14]=[C:13]([C:17]#[C:18][CH2:19][CH2:20][O:21][S:40]([CH3:39])(=[O:42])=[O:41])[CH:12]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5360545SodiumHCID 86673063HCID 86673063, compound

Product 1

HCID 89107007HCID 89107007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold solution of 7-(4-Hydroxy-but-1-ynyl)-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (tert-butyl protected oxime of example 52) (200 mg, 0.485 mmol) and triethylamine (0.15 ml, 1.067 mmol) in dichloromethane (3 ml) was added dropwise methanesulfonyl chloride (75 μl, 0.970 mmol). The reaction mixture was stirred for 1.5 hours at 0° C. and poured onto a saturated solution of sodium hydrogenocarbonate. The product was extracted with dichloromethane, washed with brine, dried over sodium sulfate and concentrated to dryness to yield methanesulfonic acid 4-{4-[(E)-tert-butoxyimino]-2-isoquinolin-3-yl-4H-chromen-7-yl}-but-3-ynyl ester. The methansulfonic ester was dissolved in dimethylformamide (4 ml) and treated with potassium carbonate (201 mg, 1.46 mmol) and methyl piperazine (73 mg, 0.728 mmol) and the mixture was stirred at 40° C. for 20 hours. The mixture was poured onto a saturated solution of sodium hydrogenocarbonate. The reaction mixture was extracted with dichloromethane, washed with water, brine, dried over sodium sulfate and absorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-45%) to yield 7-(but-3-en-1-ynyl)-2-Isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (156 mg, 82%) as a yellow solid.

Workup

  1. extractionThe product was extracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-60d8a093c1fb400da764f005a7f02d62
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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