Formaldehyde → HCID 10041531, compound

HRID 2377683Notes

Reaction equation

HRID 2377683 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[N:10]1([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:24]([O-])(=O)C.[Na+].C=O.[OH-].[Na+]>O.C(O)(=O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH2:24][N:13]1[CH2:14][CH2:15][N:10]([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:11][CH2:12]1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 2735875N-(2-Cyanophenyl)piperazine

Product 1

HCID 10041531HCID 10041531, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1H-pyrrolo[2,3-b]pyridine (47 mg, 0.40 mmol), 2-(1-piperazinyl)benzonitrile (65 mg, 0.48 mmol), sodium acetate (72 mg, 0.53 mmol), and formaldehyde (0.48 mmol) were combined in water and glacial acetic acid (1:2, 1 mL) and stirred at room temperature for 18 hours. The mixture was treated with a solution of 2M NaOH and concentrated under reduced pressure. The residue was treated with hot methanol. The methanol was filtered and the filter cake was washed with cold methanol to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.62 (m, 4H) 3.14 (m, 4H) 4.03 (s, 2H) 5.60 (s, 1H) 7.09 (m, 3H) 7.61 (m, 2H) 8.06 (dd, J=8.31, 1.53 Hz, 1H) 8.20 (dd, J=4.75, 1.70 Hz, 1H). (ESI) m/z 318 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with hot methanol
  3. filtrationThe methanol was filtered
  4. washthe filter cake was washed with cold methanol

Sources & evidence

ORD record
ord-5b6f6e342f3d415b807a6fb88164844e
Source dataset
uspto-grants-2008_12
Patent number
US07470691B2

Reaction notes

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