Acetic Acid → HCID 68294816, compound

HRID 1909335Notes

Reaction equation

HRID 1909335 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:17]([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[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CO.C(O)(=O)C.[BH3-]C#N.[Na+]>>[CH2:30]([N:14]1[CH2:15][CH2:16][CH:11]([N:8]2[C:9]3[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]([C:17]([NH:19][CH2:20][C:21]4[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=4[CH3:27])=[O:18])[C:5]=3[CH:6]=[N:7]2)[CH2:12][CH2:13]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 68294878HCID 68294878, compound

Product 1

HCID 68294816HCID 68294816, compound

Procedure

To a stirred solution of 6-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-(piperidin-4-yl)-1H-indazole-4-carboxamide (1 equiv.) and benzaldehyde (1.5 equiv.) in methanol (5 mL per 0.3 mmol), acetic acid (1 equiv.) was added and reaction stirred at room temperature for 5 h. Then NaBH3CN (1 equiv.) was added and the reaction stirred overnight. On completion, the solvent was removed under reduced pressure and the residue purified by column chromatography (27%). LCMS: 548.10 (M+1)+; HPLC: 99.16% (@ 254 nm) (Rt;5.349); 1H NMR (DMSO-d6, 400 MHz) δ 11.51 (s, 1H), 8.59 (t, 1H, J=4.8 Hz), 8.36 (s, 1H), 8.25 (s, 1H), 7.69 (d, 1H, J=1.2 Hz), 7.34 (d, 4H, J=4.4 Hz), 7.27-7.24 (m, 1H), 5.87 (s, 1H), 4.70 (m, 1H), 4.33 (d, 2H, J=4.8 Hz), 3.55 (s, 2H), 2.93 (d, 2H, J=10 Hz), 2.30-2.20 (m, 2H), 2.19 (s, 3H), 2.12 (s, 3H), 2.09 (m, 2H), 1.87 (m, 2H).

Workup

  1. customreaction
  2. stirringthe reaction stirred overnight
  3. customOn completion, the solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography (27%)

Sources & evidence

ORD record
ord-813bab3fe154440eb4d56c503b88b2dd
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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