Methanol → HCID 178474068, compound

HRID 2402466Notes

Reaction equation

HRID 2402466 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][C:10]([C:23]3[NH:27][N: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.C(Cl)Cl.N1C=CC=CC=1.[C:37](OC(=O)C)(=[O:39])[CH3:38].CO.O.C(=O)(O)[O-].[Na+]>>[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][N: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 7

HCID 887MethanolHCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178509409HCID 178509409, compound

Product 1

HCID 178474068HCID 178474068, compoundYield 52%

Procedure

To a solution of 2-(2-aminopyridin-4-yl)-4-(2,4-dichlorophenyl)-5-(1H-1,2,3-triazol-5-yl)thiophene-3-carbonitrile (0.048 g, 0.12 mmol) in DCM (4 mL, 60 mmol) was added Pyridine (0.470 mL, 5.81 mmol) and Acetic anhydride (329 uL, 3.48 mmol) and the mixture was stirred at rt overnight. The mixture was concentrated and the residue was dissolved in MeOH (2.0 mL, 49 mmol) and Water (0.3 mL, 20 mmol). Sodium bicarbonate (0.5 g, 6 mmol) was added to the above mixture. The mixture was stirred at rt for 30 min. The reaction mixture was concentrated and the residue was dissolved in EtOAc and MeOH. The solid was filtered out. The organic solution was evaporated to dryness, purified by column chromatography and then further by HPLC to afford pure title compound (27 mg, 52%). LC/MS (FA) ES+ 455, 457; ES− 453, 455. 1H-NMR (400 MHz, DMSO-d6) δ: 8.59 (1H, d, J=0.75 Hz), 8.51 (1H, d, J=5.29 Hz), 7.93 (1H, d, J=1.09 Hz), 7.54 (1H; dd, J=5.25, 1.76 Hz), 7.23 (1H, s), 7.64 (2H, d, J=1.92 Hz), 10.80 (1H, s), 2.13 (3H, s), 2.07 (1H, s)

Workup

  1. concentrationThe mixture was concentrated
  2. stirringThe mixture was stirred at rt for 30 min
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in EtOAc
  5. filtrationThe solid was filtered out
  6. customThe organic solution was evaporated to dryness
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-d80258a2329a4aff83f1a363538d0f5d
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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