1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 86609476, compound

HRID 1171740Notes

Reaction equation

HRID 1171740 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH:15]=[CH:14][C:13](/[CH:16]=[C:17]2\[CH2:18][N:19]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:21][CH:22]\2O)=[N:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:43]([OH:46])(=[S:45])[CH3:44].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:43]([S:45][CH:22]1[CH2:21][CH2:20][N:19]([C:24]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:18]/[C:17]/1=[CH:16]\[C:13]1[CH:14]=[CH:15][N:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[N:12]=1)(=[O:46])[CH3:44]

Participants

6

Reactant 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138996HCID 23138996, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86609476HCID 86609476, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-({1-[2-(t-butoxycarbonylamino)ethyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (3.67 g) in N,N-dimethylformamide (50 ml) were added thioacetic acid (4.6 ml) and N,N-dimethylformamide dineopentylacetal (18 ml). The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride successively, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel using a mixture of ethyl acetate and hexane (1:9 to 1:1) as the eluent to afford crude (E)-4-(acetylsulfanyl)-3-({1-[2-(t-butoxycarbonylamino)ethyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidine (4.29 g) as a brown oil. To a solution of the above oil in dichloromethane (50 ml) was added trifluoroacetic acid (1.5 ml) at 0° C. The resulting mixture was stirred at room temperature for 30 minutes, and the solvent was removed in vacuo. The residue was purified twice by chromatography on silica gel using a mixture of methanol and dichloromethane (1:99 to 7:93) as the eluent to afford the title compound as a brown oil (1.46 g, overall yield: 37%).

Workup

  1. washThe organic layer was washed with water and saturated aqueous sodium chloride successively
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by chromatography on silica gel using
  5. additiona mixture of ethyl acetate and hexane (1:9 to 1:1) as the eluent

Sources & evidence

ORD record
ord-d27bf8c458a0418780ce4e00852aaf30
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…