Hydrochloric Acid → HCID 178509374, compound

HRID 1497269Notes

Reaction equation

HRID 1497269 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]2[NH:7]C(=O)[O:9][C:10](=O)[C:5]=2[CH:4]=1.[CH:17]1([C:22](=O)[CH2:23][C:24]#[N:25])[CH2:21][CH2:20][CH2:19][CH2:18]1.C(N(CC)CC)C.Cl>CN(C=O)C>[CH:17]1([C:22]2[C:23]([C:24]#[N:25])=[C:10]([OH:9])[C:5]3[C:6](=[CH:13][CH:14]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=3)[N:7]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 135921183-Cyclopentyl-3-oxopropanenitrileHCID 538670346-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 178509374HCID 178509374, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-trifluoromethyl-1H-benzo[d][1,3]oxazine-2,4-dione (1.5 g, 4.22 mmol), 3-cyclopentyl-3-oxopropanenitrile (579 mg, 4.22 mmol), triethylamine (5.98 g, 8.23 ml, 59.1 mmol) and DMF (638 μl) was stirred for 72 h at room temperature. 1N HCl was added and the reaction mixture was extracted with EtOAc. The combined extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was triturated in EtOAc (8 ml) for 3 h. The solid was filtrated off and washed two times with EtOAc to afford the title compound (421 mg, 24%) as white solid. MS (ESI): 307.5 (M+H)+.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe remaining residue was triturated in EtOAc (8 ml) for 3 h
  6. filtrationThe solid was filtrated off
  7. washwashed two times with EtOAc

Sources & evidence

ORD record
ord-b73b9ff0c188407596b60380bb2ed983
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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