HCID 86671480, compound → HCID 68313039, compound

HRID 1530698Notes

Reaction equation

HRID 1530698 reaction equation
[CH:1]1([CH2:4][C:5]([O:18][C:19]2[CH:41]=[CH:40][C:22]3[C:23]4[N:27]([CH2:28][CH2:29][O:30][C:21]=3[CH:20]=2)[CH:26]=[C:25]([C:31]2[N:32]([CH:37]([CH3:39])[CH3:38])[N:33]=[C:34]([CH3:36])[N:35]=2)[N:24]=4)([CH2:12]OS(C)(=O)=O)[CH2:6]OS(C)(=O)=O)[CH2:3][CH2:2]1>C(N)C1C=CC=CC=1>[CH2:23]([N:24]1[CH2:6][C:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)([O:18][C:19]2[CH:41]=[CH:40][C:22]3[C:23]4[N:27]([CH2:28][CH2:29][O:30][C:21]=3[CH:20]=2)[CH:26]=[C:25]([C:31]2[N:32]([CH:37]([CH3:39])[CH3:38])[N:33]=[C:34]([CH3:36])[N:35]=2)[N:24]=4)[CH2:12]1)[C:22]1[CH:40]=[CH:41][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 86671480HCID 86671480, compound

Product 1

HCID 68313039HCID 68313039, compound

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

A solution of methanesulfonic acid 2-cyclopropylmethyl-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-methanesulfonyloxypropyl ester from Example 283 (90 mg, 0.1476 mmol) in benzylamine (1 mL) was heated at 180° C. for 2.5 h using microwave irradiation. After cooling to RT, the crude reaction mixture was purified by column chromatography (C18, gradient 30-65% 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 (65 mg, 84%). LCMS (Method B): RT 2.66 min [M+H]+ 525

Workup

  1. custommicrowave irradiation
  2. customthe crude reaction mixture
  3. customwas purified by column chromatography (C18, gradient 30-65% 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 (65 mg, 84%)
  6. customRT 2.66 min [M+H]+ 525

Sources & evidence

ORD record
ord-946a235e41264b799e82bbd003ba082c
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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