3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate → N-((1,2-dihydro-6-methyl-2-oxo-4-propylpyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-indazole-4-carboxamide

HRID 85498Notes

Reaction equation

HRID 85498 reaction equation
[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:14]=[C:15]4[CH:21]=[CH:20][NH:19][C:16]4=[N:17][CH:18]=3)[CH:9]=[C:8]([C:22]([OH:24])=O)[C:7]=2[C:6]([CH3:25])=[N:5]1)([CH3:3])[CH3:2].[NH2:26][CH2:27][C:28]1[C:29](=[O:38])[NH:30][C:31]([CH3:37])=[CH:32][C:33]=1[CH2:34][CH2:35][CH3:36]>>[CH3:37][C:31]1[NH:30][C:29](=[O:38])[C:28]([CH2:27][NH:26][C:22]([C:8]2[C:7]3[C:6]([CH3:25])=[N:5][N:4]([CH:1]([CH3:3])[CH3:2])[C:12]=3[CH:11]=[C:10]([C:13]3[CH:14]=[C:15]4[CH:21]=[CH:20][NH:19][C:16]4=[N:17][CH:18]=3)[CH:9]=2)=[O:24])=[C:33]([CH2:34][CH2:35][CH3:36])[CH:32]=1

Participants

3

Reactant 2

HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 674684941-isopropyl-3-methyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-indazole-4-carboxylic acid

Product 1

HCID 54596370N-((1,2-dihydro-6-methyl-2-oxo-4-propylpyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-indazole-4-carboxamide

Procedure

The title compound was prepared in the same manner as described for example 80 (step c) from 1-isopropyl-3-methyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-indazole-4-carboxylic acid (50 mg, 0.149 mmol) and 3-(aminomethyl)-6-methyl-4-propylpyridin-2(1H)-one (26 mg, 0.149 mmol) wherein the contents were stirred at RT for 5 h. The crude product was washed with DCM, filtered, and dried to afford the title compound as an off-white solid. (48 mg, 64%). 1H NMR (DMSO-d6, 400 MHz): 0.930 (t, J=7.6 Hz, 3H), 1.468 (d, J=6.4 Hz, 6H), 1.544-1.601 (m, 2H), 2.123 (s, 3H), 2.452 (s, 3H), 2.501 (s, 2H), 4.394 (d, J=4 Hz, 2H), 5.060-5.093 (m, 1H), 5.902 (s, 1H), 6.526 (s, 1H), 7.420 (s, 1H), 7.528 (s, 1H), 7.996 (s, 1H), 8.348 (s, 1H), 8.445 (s, 1H), 8.656 (s, 1H), 11.490 (brs, 1H), 11.735 (brs, 1H). LCMS (ES+) m/z: 497.49

Workup

  1. customThe title compound was prepared in the same manner
  2. washThe crude product was washed with DCM
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-856e993a1a064add9e0219a711013e04
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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