1,4-Dioxane → HCID 24804387, compound

HRID 1624995Notes

Reaction equation

HRID 1624995 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2I)[C:5]1=[O:15].[NH2:16][CH2:17][C:18]1([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[O:26]1CCOC[CH2:27]1>CO>[OH:25][C:18]1([CH2:17][NH:16][C:27]([C:10]2[C:11]3[CH:12]=[CH:13][N:4]([CH2:3][CH2:2][OH:1])[C:5](=[O:15])[C:6]=3[CH:7]=[CH:8][CH:9]=2)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 184386481-(Aminomethyl)cycloheptan-1-olHCID 67203524HCID 67203524, compound

Product 1

HCID 24804387HCID 24804387, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Into a 5 ml microwave reaction vial was combined 2-(2-hydroxyethyl)-5-iodoisoquinolin-1(2H)-one (200 mg, 0.000635 mol), 1-(aminomethyl)cycloheptanol (273 mg, 0.00190 mol) molybdenum hexacarbonyl (168 mg, 0.000635 mol) palladium acetate (10 mg, 0.00006 mol) 1,8-diazabicyclo[5.4.0]undec-7-ene (0.285 mL, 0.00190 mol) and 1,4-dioxane (3 mL, 0.03 mol). The mixture was subjected to microwave heating at 80° C. for 10 minutes. Methanol (1.5 ml) was added and the reaction mixture was filtered through a syringe filter and the filtrate concentrated. The mixture was purified by prep HPLC using a Phenomenex C18 Axia packed xolumn at PH 12. The combined pure fractions were reduced in vacuo to yield the title compound as a white solid. LC/MS M+H=359.3. 1H NMR (DMSO-d6) δ: 8.36-8.26 (m, 2H), 7.81-7.78 (dd, 1H) 7.52 (t, 1H), 7.48 (d, 1H) 6.813 (d, 1H), 4.892 (t, 1H), 4.325 (t, 1H), 4.016 (t, 1H), 3.66 (t, 1H), 3.285 (d, 1H), 1.69-1.44 (m, 10H), 1.414-1.317 (m, 2H)

Workup

  1. customInto a 5 ml microwave reaction
  2. filtrationthe reaction mixture was filtered through a syringe
  3. filtrationfilter
  4. concentrationthe filtrate concentrated
  5. customThe mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-e7f01d4cb15c400687b4f57b06585260
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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