Diisopropylethylamine → {3-[3-(2-Methoxyethoxy)-1,2,4-oxadiazol-5-yl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}-(thiomorpholin-4-yl)methanone

HRID 661303Notes

Reaction equation

HRID 661303 reaction equation
[N:1]1([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:26](O)=[O:27])[CH2:10]2)=[O:8])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O[N:63]=[C:64]([O:66][CH2:67][CH2:68][O:69][CH3:70])[NH2:65]>CN(C)C=O>[CH3:70][O:69][CH2:68][CH2:67][O:66][C:64]1[N:65]=[C:26]([CH:11]2[CH2:12][CH:13]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=3)[CH2:14][N:9]([C:7]([N:1]3[CH2:6][CH2:5][S:4][CH2:3][CH2:2]3)=[O:8])[CH2:10]2)[O:27][N:63]=1

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 581165211-(Thiomorpholin-4-ylcarbonyl)-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylic acidHCID 762237802-Methoxyethyl N-hydroxyimidocarbamate

Product 1

HCID 58116571{3-[3-(2-Methoxyethoxy)-1,2,4-oxadiazol-5-yl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}-(thiomorpholin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 300 mg (0.783 mmol) of the carboxylic acid from Example 56A in 10.0 ml of N,N-dimethylformamide were added, at room temperature, 329 mg (0.864 mmol) of HATU and 0.28 ml (205 mg, 1.59 mmol) of N,N′-diisopropylethylamine, and the mixture was stirred for 30 min. Subsequently, the mixture was admixed with 106 mg (0.792 mmol) of 2-methoxyethyl N′-hydroxyimidocarbamate from Example 44A and stirred at room temperature overnight. The reaction solution was subsequently stirred at 120° C. for 2 h. The reaction solution was purified directly by means of preparative HPLC. Yield: 98.0 mg (26% of theory)

Workup

  1. stirringThe reaction solution was subsequently stirred at 120° C. for 2 h
  2. customThe reaction solution was purified directly by means of preparative HPLC

Sources & evidence

ORD record
ord-8edc3a2083654b4ab5cffd0a6e85b696
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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