Triethylamine → HCID 86671455, compound

HRID 1530442Notes

Reaction equation

HRID 1530442 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]([CH3:30])([CH2:27][CH2:28][OH:29])[CH2:25][OH:26])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:31])=[N:5]1)([CH3:3])[CH3:2].CCN(CC)CC.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>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]([CH3:30])([CH2:25][O:26][S:40]([CH3:39])(=[O:42])=[O:41])[CH2:27][CH2:28][O:29][S:40]([CH3:39])(=[O:42])=[O:41])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:31])=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68312697HCID 68312697, compound

Product 1

HCID 86671455HCID 86671455, 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-methylbutane-1,4-diol (14 mg, 0.0318 mmol) and Et3N (13 uL, 0.095 mmol) in DCM (2 mL) at 0° C. was added methanesulfonyl chloride (6.0 uL, 0.080 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 Methanesulfonic acid 3-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-4-methanesulfonyloxy-3-methylbutyl ester as a colorless gum (23 mg, quantitative). LCMS: RT 2.99 min [M+H]+ 584.1

Workup

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

Sources & evidence

ORD record
ord-d6cab0df76784c13812201786a43e1ea
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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