Triethylamine → HCID 90466707, compound

HRID 1753237Notes

Reaction equation

HRID 1753237 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19](O)=[O:20])=[CH:11]2)=[CH:7][C:6]([C:22]([F:25])([F:24])[F:23])=[CH:5][N:4]=1.Cl.[F:27][CH2:28][CH2:29][NH2:30].C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>ClCCl.O>[F:27][CH2:28][CH2:29][NH:30][C:19]([C:12]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:18]2[N:10]([CH2:9][C:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([C:22]([F:23])([F:25])[F:24])[CH:7]=2)[CH:11]=1)=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 111923Propylphosphonic anhydrideHCID 117818496HCID 117818496, compound

Product 1

HCID 90466707HCID 90466707, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

See FIG. 19(a). To a stirred solution of 1-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (60 mg, 0.177 mmol) in dichloromethane (5 mL) were added 2-fluoroethan-1-amine hydrochloride (26 mg, 0.26 mmol), triethylamine (0.053 g, 0.531 mmol) and T3P (0.33 g, 0.531 mmol) and reaction mixture was stirred for 16 h at room temperature. Then the reaction mixture was poured in to water and extracted with dichloromethane. The reaction mixture was poured into water and extracted with dichloromethane. The combined organic layer was washed with water,brine and solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using silica gel column chromatography to afford N-(2-fluoroethyl)-1-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide as a white solid. Yield: 15 mg. (22.3%). ES+MS m/z: 397. 1H NMR (400 MHz, DMSO-d6): δ ppm 3.66-3.70 (m, 2H), 3.72-3.76 (m, 2H), 4.00 (s, 3H), 4.50-4.52 (m, 2H), 4.62-4.64 (m, 2H), 5.76 (s, 2H), 7.30-7.33 (m, 1H), 7.92 (s, 1H), 8.11 (d, 1H, J=8.3 Hz), 8.32 (s, 1H), 8.50-8.52 (m, 1H), 8.66-8.67 (m, 1H), 8.94 (t, 1H, J=5.6 Hz).

Workup

  1. extractionextracted with dichloromethane
  2. additionThe reaction mixture was poured into water
  3. extractionextracted with dichloromethane
  4. washThe combined organic layer was washed with water,brine and solvent
  5. customwas evaporated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67c7e657819b4e7fbd41c30596c6d014
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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