Triethylamine → HCID 90466564, compound

HRID 1753227Notes

Reaction equation

HRID 1753227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([N:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20](O)=[O:21])=[CH:12]1)[CH3:10].[F:23][CH2:24][CH2:25][NH2:26].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([N:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]([NH:26][CH2:25][CH2:24][F:23])=[O:21])=[CH:12]1)[CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99962-FluoroethylamineHCID 111923Propylphosphonic anhydrideHCID 1178188091H-Pyrrolo[3,2-b]pyridine-3-carboxylic acid, 1-[1-(2,6-difluorophenyl)ethyl]-

Product 1

HCID 90466564HCID 90466564, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

See FIG. 16(a). 1-(1-(2,6-difluorophenyl)ethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.090 g, 0.30 mmol), 2-fluoroethanamine (0.019 g, 0.30 mmol) and triethylamine (0.166 mL, 1.19 mmol) was taken in DCM (15 mL) under N2 and stirred. After 5 min, 1-Propanephosphonic acid cyclic anhydride (0.379 g, 1.19 mmol) was added. The resulting reaction was stirred at rt for 40 min. LCMS analysis showed formation of required product. Reaction was diluted with DCM and water. DCM layer was extracted and washed with brine and dried over sodium sulphate and concentrated. Purification was done on Waters RP system to get product 1-(1-(2,6-difluorophenyl)ethyl)-N-(2-fluoroethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (0.040 g, 38.7%) as a solid. ES+MS m/z: 348.40. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.05 (d, J=6.97 Hz, 3 H ) 3.67 (q, J=5.21 Hz, 1 H ) 3.71-3.82 (m, 1 H ) 4.49 (t, J=4.90 Hz, 1 H ) 4.65 (t, J=4.99 Hz, 1 H ) 6.22 (q, J=7.16 Hz, 1 H ) 7.13 (t, J=8.57 Hz, 2 H ) 7.29 (dd, J=8.48, 4.71 Hz, 1 H ) 7.34-7.52 (m, 1 H ) 7.80 (d, J=8.29 Hz, 1 H ) 8.41 (s, 1 H ) 8.50 (d, J=4.71 Hz, 1 H) 8.92 (t, J=5.75 Hz, 1 H ).

Workup

  1. customThe resulting reaction
  2. stirringwas stirred at rt for 40 min

Sources & evidence

ORD record
ord-19f958a9ed704a5e97705ce44ffdbc57
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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