Ethylamine → HCID 73775522, compound

HRID 712107Notes

Reaction equation

HRID 712107 reaction equation
O[CH:2]([C:4]1[N:15]([C@@H:16]2[CH2:21][O:20][C@@H:19]([CH2:22][C:23]#[N:24])[CH2:18][CH2:17]2)[C:7]2=[C:8]3[S:14][CH:13]=[CH:12][C:9]3=[N:10][CH:11]=[C:6]2[N:5]=1)[CH3:3].C(N)C.COCCN(S(F)(F)[F:38])CCOC>C(Cl)Cl>[F:38][CH:2]([C:4]1[N:15]([C@@H:16]2[CH2:21][O:20][C@@H:19]([CH2:22][C:23]#[N:24])[CH2:18][CH2:17]2)[C:7]2=[C:8]3[S:14][CH:13]=[CH:12][C:9]3=[N:10][CH:11]=[C:6]2[N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86717559HCID 86717559, compound

Product 1

HCID 73775522HCID 73775522, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled mixture of {(2R,5S)-5-[2-(1-hydroxyethyl)-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl]tetrahydro-2H-pyran-2-yl}acetonitrile (8.0 mg, 0.023 mmol) in methylene chloride (0.2 mL) was added 2-methoxy-N-(2-methoxyethyl)-N-(trifluoro-44)-sulfanyl)ethanamine (4.7 μL, 0.026 mmol) (Deoxo-Fluor). The resulting mixture was warmed to room temperature and stirred overnight. Additional Deoxo-Fluor (5 μL) was added. After 6 h, the reaction was quenched with a few drops of water then concentrated. The residue was purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give 1.6 mg (20%) of the desired product. LCMS calculated for C17H18FN4OS (M+H)+: m/z=345.1. Found: 345.0.

Workup

  1. waitAfter 6 h
  2. customthe reaction was quenched with a few drops of water
  3. concentrationthen concentrated
  4. customThe residue was purified
  5. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-6a8dee912aec4b768fc8a703795496a5
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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