Triethylamine → HCID 86671479, compound

HRID 1530690Notes

Reaction equation

HRID 1530690 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]([O:23][C:24]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)([CH2:27][OH:28])[CH2:25][OH:26])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:35])=[N:5]1)([CH3:3])[CH3:2].CCN(CC)CC.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C(Cl)Cl>[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]([O:23][C:24]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)([CH2:27][O:28][S:44]([CH3:43])(=[O:46])=[O:45])[CH2:25][O:26][S:44]([CH3:43])(=[O:46])=[O:45])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:35])=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68312658HCID 68312658, compound

Product 1

HCID 86671479HCID 86671479, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-phenylpropane-1,3-diol (115 mg, 0.242 mmol) and Et3N (101 μL, 0.725 mmol) in DCM (15 mL) cooled at 0° C. was added methanesulfonyl chloride (47 μL, 0.605 mmol) and stirring at RT was continued for 1.5 h. The mixture was diluted with DCM, washed with a saturated solution of NaHCO3, followed by water, then dried (Na2SO4) and concentrated in vacuo The resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% MeOH in DCM) affording the title compound (124.5 mg, 81%) as a colourless gum. LCMS (Method J): RT 3.26 min [M+H]+ 632

Workup

  1. washwashed with a saturated solution of NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo The resulting residue
  4. customwas purified by column chromatography (Si-PCC, gradient 2-8% MeOH in DCM)

Sources & evidence

ORD record
ord-d0e06892e1884617969645c4e4514542
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…