3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one → 6-chloro-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

HRID 1476432Notes

Reaction equation

HRID 1476432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=O)[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.[NH2:19][CH2:20][C:21]1[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=1[CH3:27]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:19][CH2:20][C:21]2[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])=[O:18])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 674667106-chloro-1-cyclopentyl-1H-indazole-4-carboxylic acid

Product 1

HCID 545972316-chloro-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

Procedure

The title compound was prepared in the same manner as described for example 3 (step c) from 6-chloro-1-cyclopentyl-1H-indazole-4-carboxylic acid (0.12 g, 0.453 mmol) and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (0.128 g, 0.680 mmol), wherein the stir time was 12 h. The crude product was purified by silica gel chromatography (eluent: 5-85% gradient chloroform (containing 10% 2M Ammonia in methanol) and dichloromethane). The isolated product was concentrated from MTBE to afford an off-white solid that was dried in hi-vac oven for 6 h. The final product was collected as 0.165 g (89%); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62-1.74 (m, 2H) 1.81-1.91 (m, 2H) 1.91-2.02 (m, 2H) 2.06-2.17 (m, 5H) 2.20 (s, 3H) 4.34 (d, J=4.80 Hz, 2H) 5.16-5.28 (m, 1H) 5.88 (s, 1H) 7.60 (d, J=1.52 Hz, 1H) 8.05 (s, 1H) 8.37 (s, 1H) 8.61 (t, J=4.93 Hz, 1H) 11.54 (s, 1H); LC-MS (ES) m/z=398.8 [M+H]+

Workup

  1. customThe crude product was purified by silica gel chromatography (eluent: 5-85% gradient chloroform (containing 10% 2M Ammonia in methanol) and dichloromethane)
  2. concentrationThe isolated product was concentrated from MTBE
  3. customto afford an off-white solid
  4. customthat was dried in hi-vac oven for 6 h
  5. customThe final product was collected as 0.165 g (89%)

Sources & evidence

ORD record
ord-85f75ff251694ec796cac3657f597c15
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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