Water → HCID 76577934, compound

HRID 240317Notes

Reaction equation

HRID 240317 reaction equation
[C:1]([C:3]1[N:4]=[C:5]2[C:18](=[N:19][OH:20])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]2=[N:7][C:8]=1[C:9]([NH2:11])=[O:10])#[N:2].[C:21](Cl)(=[O:23])[CH3:22].O>N1C=CC=CC=1>[C:1]([C:3]1[N:4]=[C:5]2[C:18](=[N:19][O:20][C:21](=[O:23])[CH3:22])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]2=[N:7][C:8]=1[C:9]([NH2:11])=[O:10])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 178510554HCID 178510554, compound

Product 1

HCID 76577934HCID 76577934, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 33 (1.0 g, 3.77 mmol) in dry pyridine (30 ml) cooled at 0° C., acetyl chloride (0.8 ml, 11.3 mmol) was added dropwise and the mixture was stirred 16 h at room temperature. Water (40 ml) was added and the precipitate was collected by filtration. The crude was purified by flash chromatography (CH2Cl2/acetone/MeOH 8:2:0.5) and triturated with Et2O/CH2Cl2/MeOH, affording 35 (251 mg, 21%) as yellow solid as single isomer. 1H NMR (300 MHz, DMSO d6): δ 8.12 (d, 1H), 7.91 (m, 2H), 7.77 (ddd, 1H), 7.43 (bs, 2H), 2.27 (s, 3H). ESI+MS: calcd for C15H9N5O3: 307.27; found: 308.1 (MH+).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customThe crude was purified by flash chromatography (CH2Cl2/acetone/MeOH 8:2:0.5)
  3. customtriturated with Et2O/CH2Cl2/MeOH

Sources & evidence

ORD record
ord-2cff47a52dbc4926a03a5d80e6a6e974
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

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