2-Chloroethyl methyl ether → HCID 67508354, compound

HRID 1400045Notes

Reaction equation

HRID 1400045 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[N:15]1([C:21]2[CH:26]=[CH:25][C:24]([C:27]34[CH2:32][CH:31]3[CH2:30][NH:29][CH2:28]4)=[CH:23][CH:22]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.[CH3:42][O:43][CH2:44][CH2:45]Cl>CN(C=O)C>[CH3:42][O:43][CH2:44][CH2:45][N:29]1[CH2:30][CH:31]2[C:27]([C:24]3[CH:23]=[CH:22][C:21]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[CH:26][CH:25]=3)([CH2:32]2)[CH2:28]1

Participants

6

Reactant 4

HCID 123162-Chloroethyl methyl etherHCID 81531DiisopropylethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 67508064HCID 67508064, compound

Product 1

HCID 67508354HCID 67508354, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of dihydrochloride salt of 1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Example XXI) (250 mg, 0.89 mmol) in anhydrous DMF (5 mL) were added DIPEA (0.63 mL, 3.56 mmol) and 2-methoxyethyl chloride (0.12 mL, 1.3 mmol) at r.t. and reaction mixture was stirred at 100° C. for 16 h. Progress of the reaction was monitored by TLC. On completion, reaction mixture was then concentrated and the crude product was purified by column chromatography (silica gel, 0.25:9.75 MeOH:CHCl3) to afford the title compound as viscous liquid (100 mg, 37%).

Workup

  1. customreaction mixture
  2. customOn completion, reaction mixture
  3. concentrationwas then concentrated
  4. customthe crude product was purified by column chromatography (silica gel, 0.25:9.75 MeOH:CHCl3)

Sources & evidence

ORD record
ord-19e85bb76bd94049beff19d2b03daf60
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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