Diisopropylethylamine → HCID 67495488, compound

HRID 1776037Notes

Reaction equation

HRID 1776037 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:18]([CH3:20])[CH3:19])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@@:10]1([CH3:17])[C:14]([OH:16])=O)=[O:8])=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[CH3:47][C@@H:48]1[CH2:53][NH:52][CH2:51][CH2:50][N:49]1[C:54]1[CH:59]=[CH:58][C:57]([N+:60]([O-:62])=[O:61])=[CH:56][N:55]=1.C(N(CC)C(C)C)(C)C>CC(N(C)C)=O>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]([C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@@:10]1([CH3:17])[C:14]([N:52]1[CH2:51][CH2:50][N:49]([C:54]2[CH:59]=[CH:58][C:57]([N+:60]([O-:62])=[O:61])=[CH:56][N:55]=2)[C@H:48]([CH3:47])[CH2:53]1)=[O:16])=[O:8])[CH:18]([CH3:20])[CH3:19]

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 58315831HCID 58315831, compoundHCID 131732218HCID 131732218, compound

Product 1

HCID 67495488HCID 67495488, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-2-methyl-pyrrolidine-2-carboxylic acid (770 mg, 2.7 mmol) was dissolved in DMA (17 mL) and HATU (1.0 g, 2.7 mmol) was added. The reaction mixture was stirred for 20 min and then (R)-2-methyl-1-(5-nitro-pyridin-2-yl)-piperazine di-HCl (700 mg, 2 mmol; Preparation 47) was added followed by N,N-diisopropylethylamine (2.0 mL, 11 mmol) and the reaction mixture was stirred at 55° C. overnight, cooled to RT, concentrated by rotary evaporation and extracted with EtOAc/water. The organic layer was washed with water, and then brine, dried over sodium sulfate, concentrated under vacuum, and purified by silica gel chromatography (0-100% ethyl acetate:hexanes) to yield the title intermediate (970 mg) as a yellow oil. (m/z): [M+H]+ calcd for C23H34N6O6 491.25 found 491.7.

Workup

  1. stirringthe reaction mixture was stirred at 55° C. overnight
  2. concentrationconcentrated by rotary evaporation
  3. extractionextracted with EtOAc/water
  4. washThe organic layer was washed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. custompurified by silica gel chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-27bc90c000514f90ba7ee7e441055cc8
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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