Formaldehyde → 4-(3-Morpholin-4-ylmethyl-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

HRID 1786684Notes

Reaction equation

HRID 1786684 reaction equation
[CH2:1]=O.[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]1[C:19](=[O:30])[NH:20][N:21]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:23]=1.[OH-].[Na+]>C(O)(=O)C.O1CCOCC1>[N:3]1([CH2:1][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9][C:10]=2[C:18]2[C:19](=[O:30])[NH:20][N:21]=[C:22]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH:23]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 1356875534-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

Product 1

HCID 1355057964-(3-Morpholin-4-ylmethyl-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 14 ul formaldehyde (37% solution in water) and 17 ul morpholine in 0.5 ml glacial acetic acid is added dropwise at 0° C. to 50 mg 4-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one suspended in 2.24 ml glacial acetic acid and 2.6 ml 1,4-Dioxan. The resulting mixture is stirred for 3 h at room temperature, subsequently poured into ice/water and the pH is adjusted to 13.3 with 2N Sodium Hydroxide. The product is isolated by filtration.

Workup

  1. customThe product is isolated by filtration

Sources & evidence

ORD record
ord-259b42023b664515a996f4294d8c1ae5
Source dataset
uspto-grants-2009_03
Patent number
US07507734B2

Reaction notes

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