Diisopropylethylamine → 2-[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-n-indan-1-yl-acetamide

HRID 747048Notes

Reaction equation

HRID 747048 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:7][N:6]([S:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])(=[O:10])=[O:9])[CH:5]([CH2:20][C:21]([OH:23])=O)[C:4](=[O:24])[NH:3]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C@H:59]1([NH2:68])[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[CH2:61][CH2:60]1>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1([CH3:25])[CH2:7][N:6]([S:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])(=[O:9])=[O:10])[CH:5]([CH2:20][C:21]([NH:68][CH:59]2[C:67]3[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=3)[CH2:61][CH2:60]2)=[O:23])[C:4](=[O:24])[NH:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733933(R)-(-)-1-AminoindanHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69078569(5,5-Dimethyl-3-oxo-1-(2,4,6-trimethylbenzene-sulfonyl)piperazin-2-yl)acetic acid

Product 1

HCID 597479532-[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-n-indan-1-yl-acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(R,S)yl]-acetic acid (50 mg, 0.135 mmol) was dissolved in DMF (2.5 mL) and DIEA (0.1 mL) was added to make a solution. HATU (117 mg, 0.31 mmol) was added and after stirring for two min, (R)-(−)-indanamine (0.1 mL) was added and the mixture was stirred overnight. The solution was poured into EtOAc (50 mL), washed with saturated NH4Cl (1×50 mL), 1 N HCl (1×50 mL), saturated NaHCO3 (1×50 mL), and saturated brine (1×50 mL). The organic layer was dried with Na2SO4, filtered, and concentrated in vacuo to provide a crude brown oil (140 mg). This crude oil was purified by SiO2 column chromatography (40 to 100% EtOAc in hexanes) to produce pure title compound. MS (APCI pos) 484 (M+H).

Workup

  1. stirringthe mixture was stirred overnight
  2. washwashed with saturated NH4Cl (1×50 mL), 1 N HCl (1×50 mL), saturated NaHCO3 (1×50 mL), and saturated brine (1×50 mL)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a crude brown oil (140 mg)
  7. customThis crude oil was purified by SiO2 column chromatography (40 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-544f455745ee42e79b804217634c23b5
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

Loading…