Water → HCID 68350681, compound

HRID 1854013Notes

Reaction equation

HRID 1854013 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]2[CH:32]=[N:31][N:30]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:16]=2[N:17]=[C:18]([C:20]2[CH2:21][C:22]([CH3:29])([CH3:28])[NH:23][C:24]([CH3:27])([CH3:26])[CH:25]=2)[CH:19]=1)=[O:13].[C:39](Cl)(=[O:41])[CH3:40].O.CO.C(Cl)Cl>N1C=CC=CC=1>[C:39]([N:36]1[CH2:37][CH2:38][CH:33]([N:30]2[C:16]3[N:17]=[C:18]([C:20]4[CH2:21][C:22]([CH3:28])([CH3:29])[NH:23][C:24]([CH3:26])([CH3:27])[CH:25]=4)[CH:19]=[C:14]([C:12]([NH:11][CH2:10][C:3]4[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=4[CH3:1])=[O:13])[C:15]=3[CH:32]=[N:31]2)[CH2:34][CH2:35]1)(=[O:41])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 21226129Dichloromethane methanolHCID 68295329HCID 68295329, compound

Product 1

HCID 68350681HCID 68350681, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-(piperidin-4-yl)-6-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.1 g, 0.2 mmol) was suspended in pyridine (1 mL) and acetyl chloride (0.016 g, 0.205 mmol) was added to it. The reaction mixture was stirred at room temperature for 5 h. On completion of reaction, water was added to it and extraction was carried out using 10% MeOH/DCM; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure. The residue was purified by prep HPLC to provide the desired compound (30% yield). LCMS: 560.00 (M+1)+; HPLC: 99.09% (@ 254 nm) (Rt; 4.685); 1H NMR (DMSO-d6, 400 MHz) δ 11.56 (s, 1H), 8.85 (t, 1H, J=5.2 Hz), 8.74 (s, 2H), 8.32 (s, 1H), 7.87 (s, 1H), 6.84 (s, 1H), 5.90 (s, 1H), 5.12-5.06 (m, 1H), 4.48 (d, 2H, J=12 Hz), 4.38 (d, 2H, J=5.2 Hz), 3.97 (m, 2H), 3.33-3.30 (m, 1H), 2.83 (s, 2H), 2.23 (s, 3H), 2.12 (s, 3H), 2.08 (s, 3H), 2.03-1.91 (m, 4H), 1.57 (s, 6H) 1.47 (s, 6H).

Workup

  1. additionwas added to it and extraction
  2. washthe combined organic layers were washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-98b2e93903394ae286437a92f4382e50
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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