N-(cyclopentylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-4-(methylsulfonyl)aniline → 3-{2-[(cyclopentylmethyl)amino]-5-(methylsulfonyl)phenyl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 633562Notes

Reaction equation

HRID 633562 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[C:18]2[C:26]3[C:21](=[C:22]([O:27]C)[N:23]=[CH:24][CH:25]=3)[N:20]([CH3:29])[CH:19]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCOCC1.Cl>[CH:1]1([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[C:18]2[C:26]3[CH:25]=[CH:24][NH:23][C:22](=[O:27])[C:21]=3[N:20]([CH3:29])[CH:19]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 90417402N-(cyclopentylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-4-(methylsulfonyl)aniline

Product 1

HCID 904158363-{2-[(cyclopentylmethyl)amino]-5-(methylsulfonyl)phenyl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-oneYield 34.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

The product from Example 68A, (0.021 g) in dioxane (0.5 mL) and 4N HCl in dioxane (0.5 mL) was heated at 70° C. for 24 hours, cooled, and concentrated. Purification by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%) afforded the title compound (0.007 g, 27%) as the TFA salt. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 7.64 (dd, J=8.70, 2.29 Hz, 1H) 7.44-7.46 (m, 2H) 6.93 (d, J=7.02 Hz, 1H) 6.83 (d, J=8.85 Hz, 1H) 6.24 (d, J=6.71 Hz, 1H) 4.12 (s, 3H) 3.09 (s, 3H) 3.06 (d, J=7.32 Hz, 2H) 2.10-2.17 (m, 1H) 1.61-1.69 (m, 2H) 1.51-1.58 (m, 2H) 1.44-1.50 (m, 2H) 1.15-1.24 (m, 2H). MS (ESI+) m/z 400 (M+H)+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customPurification by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%)

Sources & evidence

ORD record
ord-14cf14b0dd944e8d93743a5e57df40fd
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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