Formaldehyde → HCID 66576239, compound

HRID 2208758Notes

Reaction equation

HRID 2208758 reaction equation
N[CH2:2][CH2:3][N:4]([CH3:26])[C:5]1[C:6]([CH3:25])=[C:7]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[C:8]([NH:10][CH2:11][C:12]1[C:13](=[O:20])[NH:14][C:15]([CH3:19])=[CH:16][C:17]=1[CH3:18])=[O:9].[CH2:27]=O.[C:29]([BH3-])#[N:30].[Na+]>CO>[Cl:24][C:22]1[CH:23]=[C:5]([N:4]([CH2:3][CH2:2][N:30]([CH3:29])[CH3:27])[CH3:26])[C:6]([CH3:25])=[C:7]([CH:21]=1)[C:8]([NH:10][CH2:11][C:12]1[C:13](=[O:20])[NH:14][C:15]([CH3:19])=[CH:16][C:17]=1[CH3:18])=[O:9]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66576237HCID 66576237, compound

Product 1

HCID 66576239HCID 66576239, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-((2-Aminoethyl)(methyl)amino)-5-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methylbenzamide (0.075 g, 0.199 mmol) was dissolved in methanol (5 mL) and cooled to 0° C., formaldehyde (0.056 g, 1.86 mmol) was added. The resulting reaction mixture was stirred at the same temperature for 30 minutes then sodium cyanoborohydride (0.023 g, 0.366 mmol) was added to above reaction mixture and stirred at room temperature for 4 h. After completion, solvent was removed under reduced pressure and water added before extraction with DCM. The combined organic layers were dried, concentrated and purified by column chromatography to provide 5-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-((2-(dimethylamino)ethyl)(methyl)amino)-2-methylbenzamide (0.040 g, 50%). LCMS: 405.25 (M+1)+; HPLC: 89.93% (@ 254 nm) (Rt; 4.634); 1H NMR (DMSO-d6, 400 MHz) δ 11.47 (s, 1H), 8.21 (s, 1H), 7.08 (s, 1H), 5.85 (s, 1H), 4.24 (bs, 2H), 2.91 (t, 2H), 2.63 (s, 3H), 2.33-2.35 (m, 2H), 2.11-2.18 (m, 15H).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred at room temperature for 4 h
  3. customAfter completion, solvent was removed under reduced pressure and water
  4. additionadded before extraction with DCM
  5. customThe combined organic layers were dried
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-f6b1a5716c8449ab9b6eed3cbef0652e
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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