Trifluoroacetic acid → HCID 71273947, compound

HRID 1752470Notes

Reaction equation

HRID 1752470 reaction equation
COC1C=CC(C([NH:24][C:25]2[O:26][CH2:27][C:28]([F:55])([F:54])[C@:29]([C:35]3[N:40]=[C:39]([NH:41][C:42]([C:44]4[C:49]([CH3:50])=[CH:48][C:47]([C:51]#[N:52])=[CH:46][N:45]=4)=[O:43])[CH:38]=[CH:37][C:36]=3[F:53])([CH2:31][CH2:32][O:33][CH3:34])[N:30]=2)(C2C=CC(OC)=CC=2)C2C=CC=CC=2)=CC=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>ClCCl>[NH2:24][C:25]1[O:26][CH2:27][C:28]([F:54])([F:55])[C@:29]([C:35]2[N:40]=[C:39]([NH:41][C:42]([C:44]3[C:49]([CH3:50])=[CH:48][C:47]([C:51]#[N:52])=[CH:46][N:45]=3)=[O:43])[CH:38]=[CH:37][C:36]=2[F:53])([CH2:31][CH2:32][O:33][CH3:34])[N:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86689155HCID 86689155, compound

Product 1

HCID 71273947HCID 71273947, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-cyano-3-methyl-pyridine-2-carboxylic acid {6-[(R)-2-{[bis-(4-methoxy-phenyl)-phenyl-methyl]amino}-5,5-difluoro-4-(2-methoxy-ethyl)-5,6-dihydro-4H-[1,3]oxazin-4-yl]-5-fluoro-pyridin-2-yl}-amide (146 mg, 0.194 mmol), TFA (0.989 ml, 12.83 mmol) and triethylsilane (0.093 ml, 0.583 mmol) in dichloromethane (1.9 ml) was stirred at it for 18 hours. The reaction mixture was evaporated and the residue diluted with ethyl acetate, washed with sat. aqueous sodium bicarbonate solution, water and brine, dried over sodium sulfate, filtered and evaporated. 142 mg colourless resin. The product was chromatographed over a preparative silica gel plate (2 mm, 20×20 cm, Merck, dichloromethane/methanol 95:5) to give the title compound as a colourless foam. 74 mg (85% yield).

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue diluted with ethyl acetate
  3. washwashed with sat. aqueous sodium bicarbonate solution, water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was chromatographed over a preparative silica gel plate (2 mm, 20×20 cm, Merck, dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-5444f4e2eda14d01ab32d76667f51fb8
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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