Methanol → HCID 58094796, compound

HRID 2402478Notes

Reaction equation

HRID 2402478 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][C:10]([C:23]3[NH:27][CH:26]=[N:25][CH:24]=3)=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[C:12]=2[C:13]#[N:14])[CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.C(Cl)Cl.[C:37](OC(=O)C)(=[O:39])[CH3:38].CO.C(=O)(O)[O-].[Na+]>O>[C:13]([C:12]1[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[C:10]([C:23]2[NH:27][CH:26]=[N:25][CH:24]=2)[S:9][C:8]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:37](=[O:39])[CH3:38])[CH:7]=1)#[N:14]

Participants

8

Reactant 6

HCID 887MethanolHCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 58095066HCID 58095066, compound

Product 1

HCID 58094796HCID 58094796, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(2-aminopyridin-4-yl)-4-(2,4-dichlorophenyl)-5-(1H-imidazol-5-yl)thiophene-3-carbonitrile (16.3 mg, 0.0395 mmol) in Pyridine (130.5 mg, 1.650 mmol) and DCM (1.0 mL, 16 mmol) was added acetic anhydride (108.2 mg, 1.060 mmol). The mixture was stirred at rt overnight. The solvent was evaporated and the residue was dissolved in MeOH (4 mL, 90 mmol). Sodium bicarbonate (0.5 g, 6 mmol) was added and followed by water. The mixture was stirred for 30 min. The mixture was concentrated and the residue was dissolved in EtOAc. The organic phase was washed with water and the organic layer was separated and dried over sodium sulfate. The crude product was obtained by evaporation and the purified by column chromatography to afford pure title compound as a yellow solid (12.4 mg, 69.4%). LC/MS (AA) ES+ 454, 456; ES− 452, 454. 1H-NMR (DMSO-d6, 300 MHz) δ: 12.63-12.07 (1H, br), 10.79-10.74 (1H, s), 8.57 (1H, s), 8.48 (1H, d, J=5.2 Hz), 7.94 (1H, d, J=1.89 Hz), 7.74 (1H, d, J=0.92 Hz), 7.62 (1H, s), 7.64 (1H, d, J=1.98 Hz), 7.51 (1H, dd, J=5.3, 1.7 Hz), 6.30 (1H, d, J=0.94 Hz), 2.13 (3H, s)

Workup

  1. customThe solvent was evaporated
  2. stirringThe mixture was stirred for 30 min
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic phase was washed with water
  6. customthe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. customThe crude product was obtained by evaporation
  9. customthe purified by column chromatography

Sources & evidence

ORD record
ord-90d8374a390d4d8da14f51a17bb50e17
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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