Acetonitrile → HCID 86701182, compound

HRID 2206304Notes

Reaction equation

HRID 2206304 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].[CH2:30]([S:32]N=C=O)C.[C:36](#[N:38])C>>[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]([NH:38][CH3:36])=[S:32])[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 3

HCID 6342AcetonitrileHCID 21933416HCID 21933416, compoundHCID 69093549HCID 69093549, compound

Product 1

HCID 86701182HCID 86701182, compoundYield 59%

Conditions

Temperature
60 °C

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) and ethylthioisocyanate (10.4 mg, 0.12 mmol) were taken in 2 ml dry acetonitril and stirred at 60° C. 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 (32 mg, 59%).

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-d922b3ad33484224a18c26cb31e7677a
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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