4-(1-Pyrrolidinyl)piperidine → HCID 66558756, compound

HRID 1530551Notes

Reaction equation

HRID 1530551 reaction equation
CS(O[CH:6]([C:8]1[CH:9]=[CH:10][C:11]2[O:17][CH2:16][CH2:15][N:14]3[CH:18]=[C:19]([C:21]4[N:25]([CH:26]([CH3:28])[CH3:27])[N:24]=[CH:23][N:22]=4)[N:20]=[C:13]3[C:12]=2[CH:29]=1)[CH3:7])(=O)=O.[N:30]1([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:34][CH2:33][CH2:32][CH2:31]1>O1CCOCC1>[CH:26]([N:25]1[C:21]([C:19]2[N:20]=[C:13]3[C:12]4[CH:29]=[C:8]([CH:6]([N:38]5[CH2:39][CH2:40][CH:35]([N:30]6[CH2:34][CH2:33][CH2:32][CH2:31]6)[CH2:36][CH2:37]5)[CH3:7])[CH:9]=[CH:10][C:11]=4[O:17][CH2:16][CH2:15][N:14]3[CH:18]=2)=[N:22][CH:23]=[N:24]1)([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 86671465HCID 86671465, compound

Product 1

HCID 66558756HCID 66558756, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-10-yl)ethyl methanesulfonate from Example 146 (246 mg, 0.590 mmol) and 4-(pyrrolidin-1-yl)piperidine (435 mg, 2.82 mmol) in 1,4-dioxane (4 mL) was stirred at 90° 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 157. The enantiomers were separated by chiral HPLC (OD column, 30% EtOH (0.1% DEA) in n-hexane isocratic) to give: 52 mg of one enantiomer and 49 mg of the other (42% 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-270435add7d340bb9e3a758329452de2
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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