Iodine → HCID 71224278, compound

HRID 2090278Notes

Reaction equation

HRID 2090278 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[I:28]I.[OH-].[K+].OS([O-])=O.[Na+]>O1CCCC1.O.N1C=CC=CC=1>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([I:28])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 18451372N-[4-(4-Aminothieno[3,2-c]pyridin-3-yl)phenyl]-N'-(3-fluorophenyl)ureaHCID 23665763Sodium Bisulfite

Product 1

HCID 71224278HCID 71224278, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-(4-(4-aminothieno[3,2-c]pyridin-3-yl)phenyl)-3-(3-fluorophenyl)urea (example 49 in WO2005/10009) (12.2 g, 32.2 mmol) and pyridine (75 mL) in tetrahydrofuran (250 mL) was treated with iodine (36.8 g, 145 mmol) at room temperature. The reaction mixture was heated to 50° C. for 3.5 hours, then cooled to room temperature and treated with 20% aqueous KOH (18.1 g) followed by a 10% aqueous NaHSO3 solution (134 g) added in portions. The resulting mixture was heated to 60° C., diluted with water (366 mL), cooled to room temperature, and filtered. The wet cake was dried to provide the title compound.

Workup

  1. temperaturecooled to room temperature
  2. additionadded in portions
  3. temperatureThe resulting mixture was heated to 60° C.
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. customThe wet cake was dried

Sources & evidence

ORD record
ord-842fe2612b92437d960f80edb20596af
Source dataset
uspto-grants-2013_05
Patent number
US08436179B2

Reaction notes

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