Triethylamine → HCID 90466565, compound

HRID 1753228Notes

Reaction equation

HRID 1753228 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[CH2:7][N:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][C:15]=2[CH3:17])[C:10]([C:18](O)=[O:19])=[CH:9]1.F[CH2:25][CH2:26][NH2:27].[CH2:28](N(CC)CC)[CH3:29].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>ClCCl.O>[CH:25]1([CH2:26][NH:27][C:18]([C:10]2[C:11]3=[N:12][CH:13]=[CH:14][C:15]([CH3:17])=[C:16]3[N:8]([CH2:7][C:6]3[CH:21]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[O:22][CH3:23])[CH:9]=2)=[O:19])[CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99962-FluoroethylamineHCID 111923Propylphosphonic anhydrideHCID 117818778HCID 117818778, compound

Product 1

HCID 90466565HCID 90466565, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

See FIG. 16(b). To a stirred solution of 1-(5-fluoro-2-methoxybenzyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.22 g, 0.000699 moles) in dichloromethane (10 mL) were added 2-fluoroethan-1-amine (0.06 g, 0.000836 moles), triethylamine (0.29 ml, 0.002 moles) and T3P (1.32 ml, 0.002 moles) and the mixture was stirred for 16 h at room temperature. The reaction mixture was poured in to water and extracted with dichloromethane. The combined organic layer was washed with water, brine and the solvent was evaporated under reduced pressure. The crude was purified by flash column chromatography using 50% ethyl acetate in hexane to afford N-(cyclopropylmethyl)-1-(5-fluoro-2-methoxybenzyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide as a off-white solid. Yield-24%. ES+MS m/z: 368. 1H NMR (400 MHz, DMSO-d6) δ ppm: 0.22-0.24 (m, 2H ), 0.48-0.50 (m, 2H ), 1.05-1.09 (m, 1H ), 2.44 (s, 3H ), 3.28 (t, 2H , J=6.2 Hz), 3.86 (s, 3H ), 5.63 (s, 2H ), 5.97-6.00 (m, 1H ), 7.03-7.04 (m, 1H ), 7.12-7.14 (m, 2H ), 8.22 (s, 1H ), 8.37 (d, 1H , J=4.8 Hz), 9.01 (t, 1H , J=5.6 Hz).

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layer was washed with water, brine
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-3eb02cffba1e45faa38111458d55e007
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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