Diisopropylethylamine → HCID 70978668, compound

HRID 1754104Notes

Reaction equation

HRID 1754104 reaction equation
[F:1]/[C:2](=[CH:6]\[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)/[C:3]([OH:5])=O.[C:13]1([S:19]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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>CN(C=O)C>[F:1]/[C:2](=[CH:6]\[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)/[C:3]([NH:26][C:25]1[CH:24]=[CH:23][C:22]([S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])=[CH:28][CH:27]=1)=[O:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5166664-(Phenylsulfonyl)anilineHCID 5706478(2Z)-2-Fluoro-3-(3-pyridinyl)-2-propenoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 70978668HCID 70978668, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of (Z)-2-fluoro-3-(pyridin-3-yl)acrylic acid (100 mg, 0.598 mmol),4-(phenylsulfonyl)aniline (140 mg, 0.598 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (341 mg, 0.897 mmol), DIEA (232 mg, 1.795 mmol) in DMF (Volume: 10 ml) was stirred at RT for overnight, removed DMF, extracted with EtOAc, washed with 1N NaOH, brine, dried and the biotage purification afforded the product (51 mg, 23%).

Workup

  1. customremoved DMF
  2. extractionextracted with EtOAc
  3. washwashed with 1N NaOH, brine
  4. customdried
  5. customthe biotage purification

Sources & evidence

ORD record
ord-5cda0dc3a8e44e00b6093044cde80f8d
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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