4-Methylmorpholine → HCID 49841904, compound

HRID 1968202Notes

Reaction equation

HRID 1968202 reaction equation
[O:1]=[C:2]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[C@@H:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][CH:15]=[C:16]([C:17](O)=[O:18])[C:9]=12)[CH2:4][CH3:5].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C)C=O>[O:1]=[C:2]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[C@H:3]([N:6]1[C:17](=[O:18])[C:16]2=[CH:15][NH:14][C:10]3[C:9]2=[C:8]([CH:13]=[CH:12][N:11]=3)[CH2:7]1)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67224698HCID 67224698, compound

Product 1

HCID 49841904HCID 49841904, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an 8 mL scintillation vial equipped for stirring was added (S)-4-((1-oxo-1-(pyrrolidin-1-yl)butan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (8.7 mg, 0.026 mmol). N,N-dimethylformamide (2 mL), HATU (12.02 mg, 0.032 mmol) and 4-methylmorpholine (3.20 mg, 0.022 mmol) were added and the solution was allowed to stir at room temperature for 1 h. The solvent was removed and the resulting residue was further purified via preparative mass trigger LC-MS (AcCN/H2O, 5-90%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow solid (1.6 mg, 19.5%). 1H NMR (500 MHz, CD3OD) δ 0.88-1.04 (m, 3 H) 1.75-1.98 (m, 4 H) 1.98-2.05 (m, 2 H) 3.43-3.50 (m, 3 H) 3.50-3.57 (m, 1 H) 5.07 (s, 2 H) 5.62 (dd, J=8.79, 6.83 Hz, 1H) 7.13 (d, J=4.88 Hz, 1 H) 7.81 (s, 1 H) 8.28 (d, J=5.37 Hz, 1 H). [M+H] calc'd for C17H20N4O2, 313; found, 313.6.

Workup

  1. customTo an 8 mL scintillation vial equipped
  2. stirringto stir at room temperature for 1 h
  3. customThe solvent was removed
  4. customthe resulting residue was further purified via preparative mass trigger LC-MS (AcCN/H2O, 5-90%)
  5. customThe fractions were collected
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f1dc63196b0242dda42ed963144e1e3d
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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