Diisopropylethylamine → HCID 70979571, compound

HRID 1754107Notes

Reaction equation

HRID 1754107 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11].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.[N:56]1[CH:61]=[CH:60][CH:59]=[C:58](/[CH:62]=[CH:63]/[C:64](O)=[O:65])[CH:57]=1>O>[N:56]1[CH:61]=[CH:60][CH:59]=[C:58]([CH:62]=[CH:63][C:64]([NH:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[O:3][C:2]([F:1])([F:21])[F:22])(=[O:12])=[O:11])=[CH:14][CH:15]=2)=[O:65])[CH:57]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70978261HCID 70978261, compound

Product 1

HCID 70979571HCID 70979571, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 50 ml of flask were added (4-(2-(trifluoromethoxy)phenylsulfonyl)phenyl)methanamine (100 mg, 0.302 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (138 mg, 0.362 mmol DIEA (117 mg, 0.905 mmol), (E)-3-(pyridin-3-yl)acrylic acid (49.5 mg, 0.332 mmol) DMF (5 ml). The mixture was stirred at RT for 16 hours. The mixture was diluted with water and back extracted with ethyl acetate (3×20 mL). The organic layers were combined and washed with water (3×20 mL). The organic was separated, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product The crude product was purified by Biotage to afford E)-3-(pyridin-3-yl)-N-(4-(2-(trifluoromethoxy)phenylsulfonyl)benzyl)acrylamide, 85 mg (61%). 1HNMR (DMSO-D6): δ 8.70 (t, 1H), 8.75 (d, 1H), 8.54 (dd, 1H), 8.21 (dd, 2H), 7.98 (dd, 1H), 7.83 (m, 2H), 7.66 (dt, 1H), 7.53 (m, 2H), 7.44 (m, 1H), 6.75 (d, 1H), 4.49 (d, 1H)

Workup

  1. extractionback extracted with ethyl acetate (3×20 mL)
  2. washwashed with water (3×20 mL)
  3. customThe organic was separated
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product The crude product
  8. customwas purified by Biotage

Sources & evidence

ORD record
ord-5bd890872dc943cf8d59d76ed6fb782b
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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