Diisopropylethylamine → n-[6-(Tert-butylamino-methyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[5,5-dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-acetamide

HRID 747049Notes

Reaction equation

HRID 747049 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.[NH2:26][C@@H:27]1[CH2:36][CH2:35][CH2:34][C:33]2[CH:32]=[C:31]([CH2:37]O)[CH:30]=[CH:29][C:28]1=2.CC[N:41]([CH:45]([CH3:47])[CH3:46])C(C)C.[CH3:48]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CCOC(C)=O>[C:45]([NH:41][CH2:37][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[CH:27]([NH:26][C:21](=[O:23])[CH2:20][CH:5]1[C:4](=[O:24])[NH:3][C:2]([CH3:1])([CH3:25])[CH2:7][N:6]1[S:8]([C:11]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=1[CH3:19])(=[O:10])=[O:9])[CH2:36][CH2:35][CH2:34]2)([CH3:47])([CH3:48])[CH3:46]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16108956[(5R)-5-Amino-5,6,7,8-tetrahydronaphthalen-2-yl]methanolHCID 69078569(5,5-Dimethyl-3-oxo-1-(2,4,6-trimethylbenzene-sulfonyl)piperazin-2-yl)acetic acid

Product 1

HCID 72373799n-[6-(Tert-butylamino-methyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[5,5-dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(R,S)-yl]-acetic acid (600 mg, 1.6 mmol)and (5(R)-amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanol (290 mg, 1.6 mmol) were dried by azeotroping with anhydrous toluene (3×1 mL) and dissolved in anhydrous DMF (10 mL). DIEA (0.55 mL, 3.2 mmol) and HATU (923 mg, 2.4 mmol) were added to the reaction and stirred for 18 h at RT. The reaction was diluted with EtOAc (30 mL), washed with dilute HCl (2×), 1N NaOH (2×), and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 5% MeOH in CH2Cl2) to provide the title compound.

Workup

  1. customby azeotroping with anhydrous toluene (3×1 mL)
  2. dissolutiondissolved in anhydrous DMF (10 mL)
  3. washwashed with dilute HCl (2×), 1N NaOH (2×), and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a residue which
  8. customwas purified by column chromatography (SiO2, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-defc9b4d229242cf841fbd2819affca2
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

Loading…