1H-Benzotriazole-1-carboxaldehyde → HCID 54091672, compound

HRID 1601716Notes

Reaction equation

HRID 1601716 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]3=[O:23])=[CH:9][C:8]=2[F:24])=[N:4][N:3]=1.N1([CH:34]=[O:35])C2C=CC=CC=2N=N1>C1COCC1>[F:24][C:8]1[CH:9]=[C:10]([N:13]2[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]2=[O:23])[CH:11]=[CH:12][C:7]=1[C:5]1[S:6][C:2]([NH:1][CH:34]=[O:35])=[N:3][N:4]=1

Participants

4

Reactant 2

HCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 53678072HCID 53678072, compound

Product 1

HCID 54091672HCID 54091672, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of the compound of Example 30 (184 mg) in dry THF (5 mL) is added 1H-benzotriazole-1-carboxaldehyde (168 mg). The reaction mixture is heated at reflux for 48 hours, cooled and concentrated. The residue is dissolved in EtOH/CH3CN, absorbed onto silica gel and purified by flash chromatography using 7% MeOH in CH2Cl2 as the eluent to yield 155 mg of the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 48 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in EtOH/CH3CN
  6. customabsorbed onto silica gel
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-47d415ac54d14a0a9165758937856486
Source dataset
uspto-grants-1999_11
Patent number
US05977373

Reaction notes

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