Triethylamine → HCID 67066769, compound

HRID 571702Notes

Reaction equation

HRID 571702 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[CH2:43]([NH:50][CH:51]1[CH2:56][CH2:55][CH2:54][N:53]([C:57]2[C:58]3[CH:65]=[CH:64][N:63]([S:66]([C:69]4[CH:75]=[CH:74][C:72]([CH3:73])=[CH:71][CH:70]=4)(=[O:68])=[O:67])[C:59]=3[N:60]=[CH:61][N:62]=2)[CH2:52]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C=O)C.CCOC(C)=O>[CH2:43]([N:50]([CH:51]1[CH2:56][CH2:55][CH2:54][N:53]([C:57]2[C:58]3[CH:65]=[CH:64][N:63]([S:66]([C:69]4[CH:70]=[CH:71][C:72]([CH3:73])=[CH:74][CH:75]=4)(=[O:68])=[O:67])[C:59]=3[N:60]=[CH:61][N:62]=2)[CH2:52]1)[C:9](=[O:11])[CH2:8][NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 66025N-PhenylglycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67066703HCID 67066703, compound

Product 1

HCID 67066769HCID 67066769, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-phenylglycine (29 mg, 0.2 mmol), HATU (75 mg, 0.2 mmol), Et3N (50 μL, 0.4 mmol) in DMF (3 mL) was added N-benzyl-1-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-amine (90 mg, 0.2 mmol). After stirring at rt for 4 h, the solution was diluted with EtOAc and washed with water, aq. citric acid and aq. NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford a residue which was purified by column chromatography (silica gel, gradient EtOAc in hexanes) to afford the title compound.

Workup

  1. washwashed with water, aq. citric acid and aq. NaHCO3
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford a residue which
  6. customwas purified by column chromatography (silica gel, gradient EtOAc in hexanes)

Sources & evidence

ORD record
ord-f02862034ca1464c9fa80a5808fae45a
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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