Methanol → HCID 58095110, compound

HRID 2282148Notes

Reaction equation

HRID 2282148 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]=[CH: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.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]=[CH: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 58094763HCID 58094763, compound

Product 1

HCID 58095110HCID 58095110, compoundYield 44%

Procedure

To a mixture of 2-(2-aminopyridin-4-yl)-4-(2,4-dichlorophenyl)-5-(1H-pyrazol-5-yl)thiophene-3-carbonitrile (0.10 g, 0.12 mmol) and Pyridine (0.3923 mL, 4.851 mmol) in DCM (0.2 mL, 3 mmol) was added Acetic anhydride (0.114 mL, 1.21 mmol) at 0° C. The ice bath was removed after 2 h and stirring was continued at rt overnight. The solvent was evaporated and the residue was stirred in MeOH (5 mL, 100 mmol) and Water (1 g, 60 mmol) containing Sodium bicarbonate (0.6112 g, 7.276 mmol). The mixture was concentrated and the residue was collected with EtOAc. The mixture was washed with brine and dried. The solvent was evaporated and the residue was purified by column chromatography to afford the title compound (0.024 g, 41%). LC/MS (FA) ES+ 454, 456. 1H NMR (400 MHz, DMSO-d6) δ: 13.28 (1H, s), 10.78 (1H, s), 8.58 (1H, s), 8.50 (1H, dd, J=5.27, 0.63 Hz), 7.93 (1H, d, J=1.71 Hz), 7.71 (1H, d, J=2.37 Hz), 7.63 (2H, dd, J=5.25, 1.77 Hz), 7.53 (1H, dd, J=5.25, 1.77 Hz), 5.49 (1H, d, J=2.38 Hz), 2.13 (3H, s)

Workup

  1. customThe ice bath was removed after 2 h
  2. customThe solvent was evaporated
  3. concentrationThe mixture was concentrated
  4. customthe residue was collected with EtOAc
  5. washThe mixture was washed with brine
  6. customdried
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2959785786a041e9a9d3252378e58b8e
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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