2-Furylglyoxylic acid → HCID 57344130, compound

HRID 1466751Notes

Reaction equation

HRID 1466751 reaction equation
OC(C(F)(F)F)=O.[C@H:8]12[CH2:14][C@H:11]([NH:12][CH2:13]1)[CH2:10][N:9]2[C:15]([C:17]1[CH:18]=[C:19]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[NH:23][N:22]=1)=[O:16].[O:36]1[CH:40]=[CH:39][CH:38]=[C:37]1[C:41](=[O:45])[C:42](O)=[O:43].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>CN(C=O)C>[F:35][C:34]1[CH:33]=[CH:32][C:19]([CH2:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:31])[NH:23][N:22]=2)=[CH:18][C:17]=1[C:15]([N:9]1[CH2:10][C@@H:11]2[CH2:14][C@H:8]1[CH2:13][N:12]2[C:42](=[O:43])[C:41]([C:37]1[O:36][CH:40]=[CH:39][CH:38]=1)=[O:45])=[O:16]

Participants

6

Reactant 4

HCID 738462-Furylglyoxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86693908HCID 86693908, compound

Product 1

HCID 57344130HCID 57344130, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-((1S,4S)-2,5-diazabicyclo[2,2,1]heptane-2-carbonyl)-4-fluorobenzyl)phthalazin-1 (2H)-one TFA salt (200 mg, 0.41 mmol), 2-(furan-2-yl)-2-oxoacetic acid (352 mg, 2.52 mmol), DIPEA (0.63 ml, 3.78 mmol), and HATU (320 mg, 0.84 mmol) were mixed in DMF (30 ml). After the resulting reaction mixture was stirred at room temperature for 60 h, the reaction mixture was partition between DCM and water (100 ml each). The aqueous phase was extracted with DCM (100 ml), and the combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine, dried over sodium sulphate, filtered, and concentrated to yield the crude product. Then the crude product was purified by column chromatography on silica gel (Petroleum ether:Ethyl Acetate=1:3) to afford the desired product (106 mg, 50.5%) as a light yellow solid.

Workup

  1. customAfter the resulting reaction mixture
  2. customthe reaction mixture was partition between DCM and water (100 ml each)
  3. extractionThe aqueous phase was extracted with DCM (100 ml)
  4. washthe combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield the crude product
  9. customThen the crude product was purified by column chromatography on silica gel (Petroleum ether:Ethyl Acetate=1:3)

Sources & evidence

ORD record
ord-256ef2246ee64712a4851298ebe5c8fa
Source dataset
uspto-grants-2015_04
Patent number
US08999985B2

Reaction notes

Loading…