Triethylamine → HCID 86671482, compound

HRID 1530711Notes

Reaction equation

HRID 1530711 reaction equation
[CH2:1]([C:5]([O:10][C:11]1[CH:33]=[CH:32][C:14]2[C:15]3[N:19]([CH2:20][CH2:21][O:22][C:13]=2[CH:12]=1)[CH:18]=[C:17]([C:23]1[N:24]([CH:29]([CH3:31])[CH3:30])[N:25]=[C:26]([CH3:28])[N:27]=1)[N:16]=3)([CH2:8][OH:9])[CH2:6][OH:7])[CH:2]([CH3:4])[CH3:3].CCN(CC)CC.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl>[CH:29]([N:24]1[C:23]([C:17]2[N:16]=[C:15]3[N:19]([CH2:20][CH2:21][O:22][C:13]4[CH:12]=[C:11]([O:10][C:5]([CH2:8][O:9][S:42]([CH3:41])(=[O:44])=[O:43])([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:6][O:7][S:42]([CH3:41])(=[O:44])=[O:43])[CH:33]=[CH:32][C:14]=43)[CH:18]=2)=[N:27][C:26]([CH3:28])=[N:25]1)([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68313016HCID 68313016, compound

Product 1

HCID 86671482HCID 86671482, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-isobutyl-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]-propane-1,3-diol (88.6 mg, 0.194 mmol) and Et3N (81.1 μL, 0.582 mmol) in DCM (10 mL) cooled at 0° C. was added methanesulfonyl chloride (37.9 μL, 0.485 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 affording the title compound as a colourless gum (quantitative). LCMS (Method B): RT 3.46 min [M+H]+ 612.

Workup

  1. washwashed with a saturated solution of NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-610fbdb668e4446b971fb58f2c72e175
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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