Trimethylpyruvic acid → HCID 57344121, compound

HRID 1466747Notes

Reaction equation

HRID 1466747 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.[CH3:36][C:37]([CH3:44])([CH3:43])[C:38](=[O:42])[C:39](O)=[O:40].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:39](=[O:40])[C:38](=[O:42])[C:37]([CH3:44])([CH3:43])[CH3:36])[CH2:10][CH2:9]1)=[O:16]

Participants

6

Reactant 4

HCID 13150Trimethylpyruvic 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 57344121HCID 57344121, compoundYield 9.4%

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), 3,3-dimethyl-2-oxobutanoic acid [1.6 g (60%), 7.39 mmol], DIPEA (3 ml, 17.4 mmol), and HATU (1.5 g, 3.92 mmol) were mixed in DMF (50 ml). After the resulting reaction mixture was stirred at room temperature for 87 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 (EA:PE=1:1) to afford the desired product (30 mg, 9.1%) 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 preparative TLC (EA:PE=1:1)

Sources & evidence

ORD record
ord-20a8ff47ea894623be407a93ac3ff3d9
Source dataset
uspto-grants-2015_04
Patent number
US08999985B2

Reaction notes

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