Dimethylamine → HCID 68313005, compound

HRID 1530569Notes

Reaction equation

HRID 1530569 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([CH:10]([C:12]2[CH:25]=[C:24]3[C:15]([O:16][CH2:17][CH2:18][N:19]4[C:23]3=[N:22][C:21]([C:26]3[N:30]([CH:31]([CH3:33])[CH3:32])[N:29]=[CH:28][N:27]=3)=[CH:20]4)=[CH:14][CH:13]=2)[CH3:11])[CH2:7]1)(=O)=O.[CH3:34][NH:35][CH3:36]>O1CCOCC1>[CH:31]([N:30]1[C:26]([C:21]2[N:22]=[C:23]3[C:24]4[CH:25]=[C:12]([CH:10]([N:8]5[CH2:7][CH:6]([N:35]([CH3:36])[CH3:34])[CH2:9]5)[CH3:11])[CH:13]=[CH:14][C:15]=4[O:16][CH2:17][CH2:18][N:19]3[CH:20]=2)=[N:27][CH:28]=[N:29]1)([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 88932538HCID 88932538, compound

Product 1

HCID 68313005HCID 68313005, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(1-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethyl)azetidin-3-yl methanesulfonate from Example 162 (70 mg, 0.15 mmol) and dimethylamine (68 mg, 1.5 mmol) in 1,4-dioxane (4 mL) was stirred at 80° C. for 16 h under nitrogen atmosphere. After concentration, the residue was purified by reverse phase Combiflash eluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3 to give 168. The enantiomers were separated by chiral HPLC (OJ-H column, 2% EtOH (0.1% DEA) in n-hexane isocratic) to give: 9 mg of one enantiomer and 5 mg of the other (23% total yield).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by reverse phase Combiflash
  3. washeluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-e2f4ce726e31454383da1ff32ae633ec
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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