Acetonitrile → HCID 24961123, compound

HRID 1038461Notes

Reaction equation

HRID 1038461 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([CH3:30])=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:23]=2)[CH:18]=1)[CH3:11].[C:31]([O-:34])([O-])=O.[K+].[K+].[CH3:37][C:38]#N>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([CH3:30])=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:25][CH2:26][N:27]([CH2:37][CH2:38][O:34][CH3:31])[CH2:28][CH2:29]3)[CH:23]=2)[CH:18]=1)[CH3:11]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 24960023HCID 24960023, compound

Product 1

HCID 24961123HCID 24961123, compoundYield 44.4%

Procedure

A mixture of Example 10 (78 mg, 0.174 mmol), 23a (48 mg, 0.348 mmol), K2CO3 (120 mg, 0.870 mmol) and KI (32 mg, 0.191 mmol) in CH3CN (10 mL) was reacted under microwave condition at 160° C. for 2 h. After the reaction was complete, the mixture was filtered and evaporated. The residue was purified by column chromatography (EA:MeOH=10:1) to afford the title compound (44 mg, 44.4% yield) as solid. 1H-NMR (300 MHz, CDCl3): δ=8.14-8.15 (d, 1H), 7.62-7.63 (d, 1H), 7.59 (s, 1H), 7.28-7.33 (m, 1H), 6.95-7.06 (dd, 1H), 6.94-6.95 (d, 1H), 6.01-6.03 (m, 1H), 4.02 (m, 1H), 3.59-3.63 (t, 2H), 3.37 (s, 3H), 3.18-3.22 (m, 2H), 2.71-2.75 (t, 2H), 2.56 (s, 3H), 2.00-2.43 (m, 6H), 1.84-1.86 (d, 3H). LC/MS [M+H]+: 507.2.

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated
  3. customThe residue was purified by column chromatography (EA:MeOH=10:1)

Sources & evidence

ORD record
ord-d8768f7f00d1422b8e29ada72109456e
Source dataset
uspto-grants-2013_10
Patent number
US08551995B2

Reaction notes

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