4-Methoxybenzaldehyde → (NZ)-N-[(4-methoxyphenyl)methylidene]-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide

HRID 589961Notes

Reaction equation

HRID 589961 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:17][C:14]3([CH2:16][CH2:15]3)[N:13]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)=[N:3][CH:2]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27](/[CH:28]=[N:21]\[S:18]([N:13]2[C:14]3([CH2:16][CH2:15]3)[CH2:17][N:10]([C:4]3[C:5]4[CH:9]=[CH:8][NH:7][C:6]=4[N:1]=[CH:2][N:3]=3)[CH2:11][CH2:12]2)(=[O:20])=[O:19])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 574100947-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide2×

Product 1

HCID 118649767(NZ)-N-[(4-methoxyphenyl)methylidene]-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide (intermediate 1) (0.46 mmol) was suspended en dry toluene (5 ml), added 4-methoxybenzaldehyde (0.46 mmol) and stirred at reflux for 48 h. The obtained reaction mixture was concentrated in vacuo on silica. The product was purified by flash chromatography on silica using EtOAc in heptane as eluent.

Workup

  1. temperatureat reflux for 48 h
  2. customThe obtained reaction mixture
  3. concentrationwas concentrated in vacuo on silica
  4. customThe product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-2c4c606c261b41569ac28625c0877318
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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