Diisopropylethylamine → HCID 50939245, compound

HRID 1971713Notes

Reaction equation

HRID 1971713 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[C:8]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([O:19][CH:20]([CH3:22])[CH3:21])[CH:17]=3)[CH2:12][CH2:11][N:10]2[C:25]=1[C:26]([OH:28])=O)([CH3:4])([CH3:3])[CH3:2].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>C1COCC1.CN1C(=O)CCC1.O>[C:1]([N:5]1[C:26](=[O:28])[C:25]2[N:10]3[CH2:11][CH2:12][C:13]4[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:19][CH:20]([CH3:21])[CH3:22])=[CH:17][C:18]=4[C:9]3=[C:8]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)[C:7]=2[CH2:6]1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58124808HCID 58124808, compound

Product 1

HCID 50939245HCID 50939245, compoundYield 51.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 55 mg of 15e and 100 μl of DiPEA in 0.5 ml of THF and 0.1 ml of NMP was treated with 50 mg of HATU. The mixture was stirred overnight and then diluted with 5 ml of water and extracted with ethyl acetate. The extract was washed with water, dried, concentrated and the crude material was purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate, to provide 27 mg of 15f. MS-ESI:

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customthe crude material was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-0355a4dab8c74a4f95c6ba46fd200ea3
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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