2,2,2-Trifluoroethanol → HCID 21064671, compound

HRID 1243795Notes

Reaction equation

HRID 1243795 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[Na].[NH2:8][C:9]1[C:17]2[C:12](=[N:13][C:14]([N:21]3[CH2:30][CH2:29][C:24]4([O:28][CH2:27][CH2:26][O:25]4)[CH2:23][CH2:22]3)=[CH:15][C:16]=2S(C)=O)[S:11][C:10]=1[C:31]([NH2:33])=[O:32]>O>[NH2:8][C:9]1[C:17]2[C:12](=[N:13][C:14]([N:21]3[CH2:22][CH2:23][C:24]4([O:28][CH2:27][CH2:26][O:25]4)[CH2:29][CH2:30]3)=[CH:15][C:16]=2[O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[S:11][C:10]=1[C:31]([NH2:33])=[O:32]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 5360545SodiumHCID 21064665HCID 21064665, compound

Product 1

HCID 21064671HCID 21064671, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 mL of 2,2,2-trifluoroethanol cooled to 0° C. was added sodium metal (0.60 g, 15 mmol), cut fresh and washed in hexanes, in small portions. The mixture was allowed to warm up to room temperature and let stir until all of the sodium metal had reacted. To the mixture was added 3-amino-6-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-methanesulfinyl-thieno[2,3-b]pyridine-2-carboxylic acid amide (1.30 g, 3.28 mmol) as a solid in one portion. The mixture was heated to 70° C. for 15 h. The mixture was cooled to room temperature and diluted with H2O. The mixture was washed with CH2Cl2 and the combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 0.940 g of 3-amino-6-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-(2,2,2-trifluoro-ethoxy)-thieno[2,3-b]pyridine-2-carboxylic acid amide as a white powder.

Workup

  1. washwashed in hexanes, in small portions
  2. customhad reacted
  3. temperatureThe mixture was heated to 70° C. for 15 h
  4. temperatureThe mixture was cooled to room temperature
  5. washThe mixture was washed with CH2Cl2
  6. dry with materialthe combined organic phase was dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-6e660154e81545179707ac45839fab06
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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