1-Tert-butylpiperazine → HCID 68313151, compound

HRID 1530716Notes

Reaction equation

HRID 1530716 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]=[C:24]([CH3:30])[N:23]=2)=[CH:16]3)=[CH:10][N:9]=1)[CH3:7])(=O)=O.[C:31]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)([CH3:34])([CH3:33])[CH3:32]>O1CCOCC1>[C:31]([N:35]1[CH2:40][CH2:39][N:38]([C@H:6]([C:8]2[N:9]=[CH:10][C:11]3[O:12][CH2:13][CH2:14][N:15]4[CH:16]=[C:17]([C:22]5[N:26]([CH:27]([CH3:29])[CH3:28])[N:25]=[C:24]([CH3:30])[N:23]=5)[N:18]=[C:19]4[C:20]=3[CH:21]=2)[CH3:7])[CH2:37][CH2:36]1)([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 35305721-Tert-butylpiperazineHCID 86671484HCID 86671484, compound

Product 1

HCID 68313151HCID 68313151, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,12-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethyl methanesulfonate (240 mg) and 1-tert-butylpiperazine (281 mg, 1.97 mmol) in dioxane (5.00 mL) was stirred at 100° C. for 16 hrs under N2 atmosphere. After removal of the solvents, the residue was purified with reverse phase Combi-flash eluting with a 20-28% gradient of CH3CN in 0.3% NH4HCO3 to afford the desired product. The isolated solid was further separated by chiral SFC (AD-H column, EtOH (0.1% DEA) isocratic) to give the two enantiomers 303 and 305.

Workup

  1. customAfter removal of the solvents
  2. customthe residue was purified with reverse phase Combi-flash
  3. washeluting with a 20-28% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-7e86bbe5a0254675b5c4ba44f936c719
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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