Acetic Anhydride → HCID 69093479, compound

HRID 2206305Notes

Reaction equation

HRID 2206305 reaction equation
[NH2:1][C:2]1[O:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH2:16])[N:12]=3)[CH:7]=[CH:6][C:5]=2[CH:4]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([Br:27])[CH:18]=2)[C:3]=1[C:28]#[N:29].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[NH2:1][C:2]1[O:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH:16][C:30](=[O:32])[CH3:31])[N:12]=3)[CH:7]=[CH:6][C:5]=2[CH:4]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([Br:27])[CH:18]=2)[C:3]=1[C:28]#[N:29]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69093549HCID 69093549, compound

Product 1

HCID 69093479HCID 69093479, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,6-Diamino-1-(3-bromo-4,5-dimethoxy-phenyl)-1H-4-oxa-5-aza-phenanthrene-2-carbonitrile (20) (45 mg, 0.1 mmol) was taken in 2 ml pyridine at 0° C., charged with acetic anhydride (11 mg, 0.11 mmol) by drop wise addition and stirred at room temperature monitoring the reaction with LC-MS. The solvent was evaporated after the completion of the reaction. The residue was separated on HPLC (high pressure liquid chromatography) (21 mm×250 mm, RP18, 5 mm) with a methanol/water gradient (5% MeOH to MeOH in 25 min, flow 21 ml/min) to get the title compound (35 mg, 71.4%).

Workup

  1. customthe reaction with LC-MS
  2. customThe solvent was evaporated
  3. customafter the completion of the reaction
  4. customThe residue was separated on HPLC (high pressure liquid chromatography) (21 mm×250 mm, RP18, 5 mm) with a methanol/water gradient (5% MeOH to MeOH in 25 min, flow 21 ml/min)

Sources & evidence

ORD record
ord-062c1ea9f58d4002ad2a449b545e7859
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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