Triethylamine → HCID 90466852, compound

HRID 1753243Notes

Reaction equation

HRID 1753243 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[N:15]=[CH:14][N:13]=3)[CH:9]=[C:8]([C:21](O)=[O:22])[C:5]2=[N:6][CH:7]=1.[F:24][CH2:25][CH2:26][NH2:27].C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>ClCCl.O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[N:15]=[CH:14][N:13]=3)[CH:9]=[C:8]([C:21]([NH:27][CH2:26][CH2:25][F:24])=[O:22])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99962-FluoroethylamineHCID 111923Propylphosphonic anhydrideHCID 117818882HCID 117818882, compound

Product 1

HCID 90466852HCID 90466852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

See FIG. 20(d). To a stirred solution of 6-bromo-1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.13 g, 0.34 mmol) in dichloromethane (10 mL), were added 2-fluoroethan-1-amine (0.06 g, 0.68 mmol), triethylamine (0.1 g, 1.02 mmol) and T3P (0.32 g, 1.02 mmol) and the mixture was stirred at RT for 16 h. Then the reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with brine and concentrated. The crude product was purified by silica gel column chromatography and subsequent PREP purification to afford 6-bromo-N-(2-fluoroethyl)-1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide as a white solid. Yield: 25 mg (17%). ES+MS m/z: 424.2 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.24 (s, 3H), 3.68 (bs, 1H), 3.75 (bs, 1H), 4.51 (bs, 1H), 4.64 (bs, 1H), 5.70 (s, 2H), 8.28 (s, 1H), 8.39 (d, 1H, J=10.9 Hz), 8.58 (s, 1H), 8.64 (bs, 2H)

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography and subsequent PREP purification

Sources & evidence

ORD record
ord-5e3c9e0c9c08423691f0765a90c19ee4
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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