2-(4-Piperidyl)-2-propanol → HCID 68313109, compound

HRID 1530547Notes

Reaction equation

HRID 1530547 reaction equation
CS(O[CH:6]([C:8]1[CH:21]=[C:20]2[C:11]([O:12][CH2:13][CH2:14][N:15]3[C:19]2=[N:18][C:17]([C:22]2[N:26]([CH:27]([CH3:29])[CH3:28])[N:25]=[CH:24][N:23]=2)=[CH:16]3)=[CH:10][CH:9]=1)[CH3:7])(=O)=O.[NH:30]1[CH2:35][CH2:34][CH:33]([C:36]([OH:39])([CH3:38])[CH3:37])[CH2:32][CH2:31]1>O1CCOCC1>[CH:27]([N:26]1[C:22]([C:17]2[N:18]=[C:19]3[C:20]4[CH:21]=[C:8]([CH:6]([N:30]5[CH2:35][CH2:34][CH:33]([C:36]([OH:39])([CH3:38])[CH3:37])[CH2:32][CH2:31]5)[CH3:7])[CH:9]=[CH:10][C:11]=4[O:12][CH2:13][CH2:14][N:15]3[CH:16]=2)=[N:23][CH:24]=[N:25]1)([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 52003212-(4-Piperidyl)-2-propanolHCID 86671465HCID 86671465, compound

Product 1

HCID 68313109HCID 68313109, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 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 methanesulfonate from Example 146 (123 mg, 0.295 mmol) in dioxane (15 mL) was added 2-(piperidin-4-yl)propan-2-ol (422 mg, 2.95 mmol). The mixture was heated at 90° C. overnight. The solvent was removed and the residue was purified by Combi-flash eluting with a 5-95% gradient of CH3CN in 0.3% NH4HCO3 to give 152. The enantiomers were separated by chiral SFC (OD-H column, 15% EtOH isocratic) to give: 17.6 mg of one enantiomer and 13.0 mg of the other (22% total yield)

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by Combi-flash
  3. washeluting with a 5-95% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-44f31930d5fc499ebc7ad6c56b6865dd
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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