Trifluoroacetic acid → HCID 178485597, compound

HRID 1053630Notes

Reaction equation

HRID 1053630 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:9]([CH:10]=NC)=[CH:8][NH:7][N:6]=1)=[O:4].C(O)(C(F)(F)F)=[O:14]>C1COCC1.O>[CH:10]([C:9]1[C:5]([C:3]([NH:2][CH3:1])=[O:4])=[N:6][NH:7][CH:8]=1)=[O:14]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178482992HCID 178482992, compound

Product 1

HCID 178485597HCID 178485597, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of product (3-B) (17.1 g, 0.1 mol) in THF (100 mL) was added drop-wise a solution of TFA (57 g, 0.5 mol) in H2O (100 mL) at rt. The reaction mixture was stirred overnight at rt. The yellow precipitate was filtered, washed with H2O, and dried in air to give crude product (3-C) (12.5 g, 82%, for two steps) as a light yellow solid. 1H NMR (300 MHz, d-DMSO): δ 13.93 (br, 1H), 10.33 (br, 1H), 8.52 (br, 1H), 8.44 (s, 1H), 2.79 (d, 3H). LC-MS (M+H)+=154.

Workup

  1. filtrationThe yellow precipitate was filtered
  2. washwashed with H2O
  3. customdried in air

Sources & evidence

ORD record
ord-1228ae367f224e9fa83bbcd65015f33c
Source dataset
uspto-grants-2016_07
Patent number
US09394256B2

Reaction notes

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