Phenylglyoxylic Acid → HCID 57344122, compound

HRID 1466748Notes

Reaction equation

HRID 1466748 reaction equation
OC(C(F)(F)F)=O.[N:8]1([C:15]([C:17]2[CH:18]=[C:19]([CH:32]=[CH:33][C:34]=2[F:35])[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)=[O:16])[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[O:36]=[C:37]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38](O)=[O:39].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:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:38](=[O:39])[C:37]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:36])[CH2:10][CH2:9]1)=[O:16]

Participants

6

Reactant 4

HCID 11915Phenylglyoxylic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86693909HCID 86693909, compound

Product 1

HCID 57344122HCID 57344122, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-(1,4-diazepane-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2H)-one TFA salt (320 mg, 0.65 mmol), 2-oxo-2-phenylacetic acid (1.4 g, 9.32 mmol), DIPEA (3 ml, 17.4 mmol), and HATU (1.8 g, 4.72 mmol) were mixed in DMF (50 ml). After the resulting reaction mixture was stirred at room temperature for 85 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 preparative TLC (Petroleum ether:Ethyl Acetate=1:1 to 1:2) to afford the desired product (140 mg, 41%) 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 preparative TLC (Petroleum ether:Ethyl Acetate=1:1 to 1:2)

Sources & evidence

ORD record
ord-b620728fad5343d3b4609342841db454
Source dataset
uspto-grants-2015_04
Patent number
US08999985B2

Reaction notes

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