Triethylamine → HCID 90466850, compound

HRID 1753241Notes

Reaction equation

HRID 1753241 reaction equation
C[C:2]1[N:10]([CH2:11][C:12]2[C:13]([O:20][CH3:21])=[N:14][C:15]([CH3:19])=[C:16]([F:18])[CH:17]=2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:22](O)=[O:23].Cl.[F:26][CH2:27][CH2:28][NH2:29].C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>ClCCl.O>[F:18][C:16]1[CH:17]=[C:12]([CH2:11][N:10]2[C:9]3[C:4](=[N:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:22]([NH:29][CH2:28][CH2:27][F:26])=[O:23])=[CH:2]2)[C:13]([O:20][CH3:21])=[N:14][C:15]=1[CH3:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 111923Propylphosphonic anhydrideHCID 117819085HCID 117819085, compound

Product 1

HCID 90466850HCID 90466850, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

See FIG. 20(b). To the stirred solution of methyl 1-((5-fluoro-2-methoxy-6-methylpyridin-3-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.15 g, 0.47 mmol) in dichloromethane (10 mL), were added 2-fluoroethan-1-amine hydrochloride (71 mg, 0.71 mmol), triethylamine (0.142 g, 1.41 mmol) and T3P (0.9 g, 1.41 mmol) and the mixture was stirred for 16 h at room temperature. Then the reaction mixture was poured into water and extracted with dichloromethane. The combined organic layer was washed with water, brine, dried over sodium sulfate, and concentrated at reduced pressure. The residue was purified by silica gel column chromatography to yield 1-((5-fluoro-2-methoxy-6-methylpyridin-3-yl)methyl)-N-(2-fluoroethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide as a white solid. Yield: 30 mg (18%). ES+MS m/z: 361 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.31 (d, 3H, J=2.9 Hz), 3.64-3.68 (m, 2H), 3.71-3.75 (m, 2H), 3.85 (s, 3H), 4.49-4.51 (m, 2H), 4.61-4.63 (m, 2H), 5.41 (s, 2H), 7.28-7.32 (m, 1H), 7.45 (d, 1H, J=9.0 Hz), 8.08-8.11 (m, 1H), 8.29 (s, 1H), 8.49-8.50 (m, 1H), 8.92 (t, 1H, J=5.8 Hz).

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6c8248ab2d3b409f97333c5d935296bb
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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