Dimethylamine → HCID 59297027, compound

HRID 886568Notes

Reaction equation

HRID 886568 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[N:23]=[C:22]([CH2:24][C:25](O)=[O:26])[CH:21]=[N:20][CH:19]=3)[CH:16]=2)[N:11]([S:28]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH:10]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:49]2[N:50]=[CH:51]C=CC=2N=N1.C(NC(C)C)(C)C.CNC>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[N:23]=[C:22]([CH2:24][C:25]([N:50]([CH3:51])[CH3:49])=[O:26])[CH:21]=[N:20][CH:19]=3)[CH:16]=2)[N:11]([S:28]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH:10]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 7912DiisopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59825100HCID 59825100, compound

Product 1

HCID 59297027HCID 59297027, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Crude {6-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrazin-2-yl}-acetic acid (0.55 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (251 mg, 0.66 mmol), and di-iso-propylamine (114.9 μL, 0.66 mmol) were dissolved in tetrahydrofuran (5 mL) and 2 M dimethylamine (412 μL, 0.825 mmol) was added. The mixture was heated to 60° C. in a capped vial for 30 minutes, cooled, diluted with ethyl acetate and washed with saturated sodium bicarbonate (1×), saturated ammonium chloride (1×) and brine (1×). The organics were dried over sodium sulfate, filtered and concentrated to yield a yellow foam (305 mg, >100%). The crude material was used without further purification in the next step.

Workup

  1. temperaturecooled
  2. washwashed with saturated sodium bicarbonate (1×), saturated ammonium chloride (1×) and brine (1×)
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-24405861da814db9860b581014f71396
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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