N-Methylethylamine → 853003-48-2

HRID 1516299Notes

Reaction equation

HRID 1516299 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:23][C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[O:17])[C:6]=2[N:7]=1.[CH3:31][NH:32][CH2:33][CH3:34].C(N(C(C)C)C(C)C)C.[F-].[Cs+]>CS(C)=O>[CH2:14]([O:13][CH2:12][CH2:11][N:10]1[C:5]2[C:4]([NH:23][C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=3)=[N:3][C:2]([N:32]([CH2:33][CH3:34])[CH3:31])=[N:7][C:6]=2[C:8]([C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[O:17])=[N:9]1)[CH3:15]

Participants

6

Reactant 4

HCID 12219N-MethylethylamineHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 57799247HCID 57799247, compound

Product 1

HCID 11465695853003-48-2Yield 57.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

The chloro compound of Step 9 (110 mg, 0.24 mmol), N-methyl-ethylamine (79 mg, 1.2 mmol), N-ethyldiisopropylamine (210 μL, 1.20 mmol) and caesium fluoride (37 mg, 0.24 mmol) were dissolved in dimethyl sulphoxide (1 mL) and the reaction mixture heated to 110° C. for 5 hours in a ReactiVial™. The reaction mixture was partitioned between ethyl acetate (10 mL) and water (10 mL) and the organic phase separated and washed with water (2×10 mL). The organic phase was then dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 99:1 to 97:3. The purified material was evaporated and dried to yield a pale yellow solid (66 mg). The PXRD pattern for the solid is shown as FIG. 14.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (10 mL) and water (10 mL)
  2. customthe organic phase separated
  3. washwashed with water (2×10 mL)
  4. dry with materialThe organic phase was then dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 99:1 to 97:3
  7. customThe purified material was evaporated
  8. customdried

Sources & evidence

ORD record
ord-43a43594b99d4b15aa0b5f39d1ca7ffe
Source dataset
uspto-grants-2012_07
Patent number
US08227475B2

Reaction notes

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