Hydrochloric Acid → 3-{2-[(cyclopropylmethyl)(methyl)amino]-5-(methylsulfonyl)phenyl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 633541Notes

Reaction equation

HRID 633541 reaction equation
[CH:1]1([CH2:4][N:5]([CH3:28])[C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]2[C:24]3[C:19](=[C:20]([O:25]C)[N:21]=[CH:22][CH:23]=3)[N:18]([CH3:27])[CH:17]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1>>[CH:1]1([CH2:4][N:5]([CH3:28])[C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]2[C:24]3[CH:23]=[CH:22][NH:21][C:20](=[O:25])[C:19]=3[N:18]([CH3:27])[CH:17]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90416403N-(cyclopropylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-N-methyl-4-(methylsulfonyl)aniline

Product 1

HCID 904160343-{2-[(cyclopropylmethyl)(methyl)amino]-5-(methylsulfonyl)phenyl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-oneYield 58.8%

Conditions

Temperature
70 °C

Procedure

The product from Example 45A (0.12 g, 0.30 mmol) and 4 M hydrogen chloride in dioxane (5 mL, 20.00 mmol) were combined and heated at 70° C. for 24 hours, cooled and concentrated. Purification by reverse phase chromatography (C18, CH3CN/water (0.1% TFA), 10-100%) afforded the title compound (0.068 g, 45%) as the TFA salt. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.91 (d, J=5.09 Hz, 1H) 7.70 (dd, J=8.48, 2.37 Hz, 1H) 7.61 (d, J=2.37 Hz, 1H) 7.54-7.56 (m, 1H) 7.21 (d, J=8.48 Hz, 1H) 6.84 (dd, J=7.12, 5.76 Hz, 1H) 6.31 (d, J=5.76 Hz, 1H) 4.11 (s, 3H) 3.15 (s, 3H) 2.77 (s, 3H) 2.74 (d, J=6.78 Hz, 2H) 0.64-0.78 (m, 1H) 0.28-0.37 (m, 2H) −0.11-−0.05 (m, 2H). MS (ESI+) m/z 386 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-97c53237d3bd48b6bcb0db097a6405b2
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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