2,2,2-Trifluoroethylamine hydrochloride → HCID 86726646, compound

HRID 1506258Notes

Reaction equation

HRID 1506258 reaction equation
[O:1]=[C:2]1[N:7]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH:14]=O)[CH2:10][CH2:9]2)[C:6]2[C:16]3[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]=3[N:18]=[CH:19][C:5]=2[C:4](=[O:31])[NH:3]1.Cl.[F:33][C:34]([F:38])([F:37])[CH2:35][NH2:36].B.N1C=CC=CC=1C.[OH-].[Na+]>CO.C(O)(=O)C>[F:33][C:34]([F:38])([F:37])[CH2:35][NH:36][CH2:14][CH:11]1[CH2:10][CH2:9][CH:8]([N:7]2[C:6]3[C:16]4[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]=4[N:18]=[CH:19][C:5]=3[C:4](=[O:31])[NH:3][C:2]2=[O:1])[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 16217944Borane;2-methylpyridineHCID 178504208HCID 178504208, compound

Product 1

HCID 86726646HCID 86726646, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

trans-4-(2,4-Dioxo-7-{[2-(trimethylsilyl)ethoxy]methyl}-2,3,4,7-tetrahydro-1H-pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidin-1-yl)cyclohexanecarbaldehyde (30.4 mg, 0.0680 mmol) in a mixture of methanol (0.5 mL) and acetic acid (50 μL) was stirred with 2,2,2-trifluoroethanamine hydrochloride (12.1 mg, 0.089 mmol) and 2-picoline borane (9.50 mg, 0.089 mmol) at room temperature for 1 day. After addition of 1 M aqueous sodium hydroxide, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel thin layer chromatography (ethyl acetate/hexane=1/1 (v/v)) to give the title compound as a colorless solid (32.3 mg, yield 90%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel thin layer chromatography (ethyl acetate/hexane=1/1 (v/v))

Sources & evidence

ORD record
ord-186cc993154f49a092b89e07f0e35a8d
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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