1,4-Dioxane → HCID 24804227, compound

HRID 1624994Notes

Reaction equation

HRID 1624994 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].[CH:16]1([CH2:23][NH2:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.N12CCCN=C1CCCCC2.[O:36]1CCOC[CH2:37]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:16]1([CH2:23][NH:24][C:37]([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:36])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 78194CycloheptylmethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67203524HCID 67203524, compound

Product 1

HCID 24804227HCID 24804227, compound

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
110 °C

Procedure

Into a 5 ml microwave reaction vessel was combined 2-(2-hydroxyethyl)-5-iodoisoquinolin-1(2H)-one (0.100 g, 0.000317 mol), cycloheptylmethanamine (100 mg, 0.0008 mol), molybdenum hexacarbonyl (80 mg, 0.0003 mol), palladium acetate (7 mg, 0.00003 mol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.1 mL, 0.001 mol) and 1,4-dioxane (1 mL, 0.02 mol). The vessel was exposed to microwave heating for 15 min at 110° C. The reaction tube was cooled to room temperature and the volatiles removed under educed pressure. The mixture was purified directly by column chromatography using an methanol:methylene chloride (0-10%) gradient. The combined pure fractions were reduced in vacuo to yield a white solid which was purified again by HPLC to afford the title compound as a white solid. 1H NMR (DMSO-d6) δ: 8.55 (t, 1H), 8.31 (d, 1H), 7.72 (dd, 1H), 7.517 (t, 1H), 7.446 (d, 1H), 6.76 (d, 1H), 4.88 (t, 1H) 4.014 (t 2H), 3.66 (q, 2H) 3.123 (t, 2H), 1.79-1.34 (m, 11H), 1.2615-1.149 (m, 2H)

Workup

  1. customInto a 5 ml microwave reaction vessel was combined
  2. temperatureThe reaction tube was cooled to room temperature
  3. customthe volatiles removed under educed pressure
  4. customThe mixture was purified directly by column chromatography
  5. customto yield a white solid which
  6. customwas purified again by HPLC

Sources & evidence

ORD record
ord-0f4bc43b03354973bfba6de617215f94
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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