Pyruvic Acid → HCID 57344126, compound

HRID 1466753Notes

Reaction equation

HRID 1466753 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]([CH3:41])[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](=[O:36])[CH3:41])[CH2:10][CH2:9]1)=[O:16]

Participants

6

Reactant 4

HCID 1060Pyruvic 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 57344126HCID 57344126, compoundYield 46.4%

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-oxopropanoic acid [0.3 ml (d=1.26), 4.29 mmol], DIPEA (1 ml, 6 mmol), and HATU (510 mg, 1.34 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=1:2) to afford the desired product (136 mg, 45.1%) as an off white 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=1:2)

Sources & evidence

ORD record
ord-e25869ef2d8c4e80b4c35e7f6c03a2ab
Source dataset
uspto-grants-2015_04
Patent number
US08999985B2

Reaction notes

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