HCID 86671478, compound → HCID 68312636, compound

HRID 1530685Notes

Reaction equation

HRID 1530685 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]([CH3:37])([CH2:31]OS(C)(=O)=O)[CH2:25]OS(C)(=O)=O)[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:38])=[N:5]1)([CH3:3])[CH3:2]>C(N)C1C=CC=CC=1>[CH2:17]([N:11]1[CH2:25][C:24]([CH3:37])([O:23][C:21]2[CH:20]=[CH:19][C:16]3[C:17]4[N:11]([CH2:12][CH2:13][O:14][C:15]=3[CH:22]=2)[CH:10]=[C:9]([C:8]2[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=[C:6]([CH3:38])[N:7]=2)[N:18]=4)[CH2:31]1)[C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:15]=1

Participants

3

Reactant 1

HCID 86671478HCID 86671478, compound

Product 1

HCID 68312636HCID 68312636, compound

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

A solution of methanesulfonic acid 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]-3-methanesulfonyloxy-2-methylpropyl ester (0.096 mmol) in benzylamine (0.5 mL) was heated at 150° C. for 1 h and then 180° C. for a further 1 h using microwave irradiation. After cooling to RT, the crude reaction mixture was purified by column chromatography (C18, gradient 15-55% MeOH in 0.5% TFA/H2O) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3/MeOH affording the title compound as a colourless gum (31 mg, 67% over two steps). LCMS (Method B): RT 2.40 min [M+H]+ 485

Workup

  1. custommicrowave irradiation
  2. customthe crude reaction mixture
  3. customwas purified by column chromatography (C18, gradient 15-55% MeOH in 0.5% TFA/H2O)
  4. washThe cartridge was washed with MeOH
  5. washthe product eluted with 0.5M NH3/MeOH affording the title compound as a colourless gum (31 mg, 67% over two steps)
  6. customRT 2.40 min [M+H]+ 485

Sources & evidence

ORD record
ord-ab9f09028448438db78fa0ec6ed45907
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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