Triethylamine → HCID 90467009, compound

HRID 1753250Notes

Reaction equation

HRID 1753250 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH3:20])[CH:18]=3)[C:13]([C:21](O)=[O:22])=[CH:12]2)[C:5]([CH3:9])=[N:6][C:7]=1[CH3:8].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:48][CH2:49][CH2:50][NH2:51].C(N(CC)CC)C>CN1C(=O)CCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH3:20])[CH:18]=3)[C:13]([C:21]([NH:51][CH2:50][CH2:49][F:48])=[O:22])=[CH:12]2)[C:5]([CH3:9])=[N:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99962-FluoroethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117819028HCID 117819028, compound

Product 1

HCID 90467009HCID 90467009, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

See FIG. 23(a). In a 25 mL thermal vial was charged with 1-((5-fluoro-2,6-dimethylpyridin-3-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (100 mg, 0.32 mmol) and HATU (146 mg, 0.38 mmol) were taken in NMP (4 mL) and stirred for 10 min at rt. Then 2-fluoroethanamine (20.13 mg, 0.32 mmol) and Triethyl amine (133 mL, 0.96 mmol) were added and stirred for 1 h at rt. The LCMS showed completion of the reaction. The reaction mixture was poured into water and extracted with chloroform. The organic layer was dried and concentrated and crude was submitted to reverse phase purification. The pure fractions were concentrated to get 1-((5-fluoro-2,6-dimethylpyridin-3-yl)methyl)-N-(2-fluoroethyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (75 mg, 65.6%) as a solid. ES+MS m/z: 359 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.37 (d, J=2.64 Hz, 3 H ) 2.42 (s, 6 H ) 3.66 (d, J=5.46 Hz, 1 H ) 3.75 (d, J=5.27 Hz, 1 H ) 4.49 (t, J=4.90 Hz, 1 H ) 4.65 (t, J=4.99 Hz, 1 H ) 5.52 (s, 2 H ) 6.85 (d, J=10.17 Hz, 1 H ) 7.86 (s, 1 H ) 8.15 (s, 1 H ) 8.34-8.46 (m, 1 H ) 8.89 (t, J=5.84 Hz, 1 H ).

Workup

  1. stirringstirred for 1 h at rt
  2. customcompletion of the reaction
  3. extractionextracted with chloroform
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customphase purification
  7. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-0ac58bfaa84a48a2813f72226fd61062
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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