Triethylamine → HCID 86671478, compound

HRID 1530684Notes

Reaction equation

HRID 1530684 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]([CH3:29])([CH2:27][OH:28])[CH2:25][OH:26])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:30])=[N:5]1)([CH3:3])[CH3:2].CCN(CC)CC.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>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]([CH3:29])([CH2:27][O:28][S:39]([CH3:38])(=[O:41])=[O:40])[CH2:25][O:26][S:39]([CH3:38])(=[O:41])=[O:40])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:30])=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68312729HCID 68312729, compound

Product 1

HCID 86671478HCID 86671478, compound

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-methylpropane-1,3-diol (79.4 mg, 0.192 mmol) and Et3N (80 uL, 0.574 mmol) in DCM (10 mL) cooled at 0° C. was added methanesulfonyl chloride (37.4 uL, 0.48 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 J): RT 2.98 min [M+H]+ 570.

Workup

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

Sources & evidence

ORD record
ord-be166830c21149709493eebc74c149bb
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…