Hydrochloric Acid → HCID 67066750, compound

HRID 571703Notes

Reaction equation

HRID 571703 reaction equation
C(O[C:6]([NH:8][CH2:9][C:10](O)=O)=[O:7])(C)(C)C.[CH3:13][N:14](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.C(N[CH:52]1CC[CH2:55][N:54]([C:58]2[C:59]3[CH:66]=[CH:65][N:64](S(C4C=CC(C)=CC=4)(=O)=O)[C:60]=3[N:61]=[CH:62][N:63]=2)[CH2:53]1)C1C=CC=CC=1.Cl>CN(C=O)C.CCOC(C)=O>[N:61]1[C:60]2[NH:64][CH:65]=[CH:66][C:59]=2[C:58]([N:54]2[CH2:53][CH2:52][CH2:10][CH:9]([NH:8][C:6](=[O:7])[CH2:13][NH2:14])[CH2:55]2)=[N:63][CH:62]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 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 67066750HCID 67066750, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)acetic acid (0.7 g, 4 mmol), HATU (1.5 g, 4 mmol), Et3N (1.1 mL, 4 mmol) in DMF (60 mL) was added N-benzyl-1-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-amine (1.8 g, 40 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 a solid. The Boc protected amine was dissolved in 1,4-dioxane (10 mL) and treated with 4 N HCl (10 equiv.) at rt for 5 h. The solvent was concentrated in vacuo to afford N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl)-2-aminoacetamide as a solid which was used without any additional purification.

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) to a solid
  7. dissolutionwas dissolved in 1,4-dioxane (10 mL)
  8. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-45f76371223542a18d5a5ac4571c5dd7
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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