Triethylamine → HCID 88932511, compound

HRID 1530445Notes

Reaction equation

HRID 1530445 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][CH:24]([CH2:27][CH:28]([CH3:31])[CH2:29][OH:30])[CH2:25][OH:26])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:32])=[N:5]1)([CH3:3])[CH3:2].CCN(CC)CC.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>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][CH:24]([CH2:25][O:26][S:41]([CH3:40])(=[O:43])=[O:42])[CH2:27][CH:28]([CH3:31])[CH2:29][O:30][S:41]([CH3:40])(=[O:43])=[O:42])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:32])=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68313136HCID 68313136, compound

Product 1

HCID 88932511HCID 88932511, 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]-4-methylpentane-1,5-diol (90 mg, 0.2038 mmol) and Et3N (85 uL, 0.6114 mmol) in DCM (10 mL) cooled at 0° C. was added methanesulfonyl chloride (40 uL, 0.51 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 4-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-5-methanesulfonyloxy-2-methylpentyl ester as a colorless gum (quantitative). LCMS: RT 3.07 min [M+H]+ 598.1

Workup

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

Sources & evidence

ORD record
ord-09aa7f5bc6fd4960aa53ae4b51239d2a
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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