Water → HCID 25195956, compound

HRID 2237266Notes

Reaction equation

HRID 2237266 reaction equation
C([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21](=[O:30])[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[O:19])=[CH:13][C:12]=2[Cl:31])[CH:7]=[CH:6][N:5]=1)(=O)N.O.[N:33]1C=CC=CC=1.FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C(I)C=CC=1)=O>CN(C=O)C>[ClH:31].[NH2:33][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21](=[O:30])[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[O:19])=[CH:13][C:12]=2[Cl:31])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 11711920HCID 11711920, compoundHCID 12041285Bistrifluoroacetoxyiodobenzene

Product 1

HCID 25195956HCID 25195956, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-(2-carbamoylpyridin-4-yloxy)-3-chlorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea (Example 90, 27 mg, 0.06 mmol) in DMF (1.0 mL) were added H2O (2.2 mg, 0.12 mmol), pyridine (0.04 mL) and bis(trifluoroacetoxy)iodobenzene (Aldrich, 39 mg, 0.09 mmol) at room temperature. The solution was allowed to stir overnight and then it was purified on prep HPLC to give the desired product, which was further converted to 1-(4-(2-aminopyridin-4-yloxy)-3-chlorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea hydrochloride (19 mg, 70% yield) by the addition of 1N HCl solution (0.5 mL). 1H NMR (DMSO-d6) δ 13.50 (s, 1H), 11.02 (s, 1H), 10.57 (s, 1H), 7.80-7.95 (m, 4H), 7.55 (m, 1H), 7.37 (m, 1H), 7.30 (m, 2H), 7.11 (m, 2H), 6.60 (m, 1H), 6.00 (s, 1H), 3.70 (s, 2H); MS(ESI+): m/z 415.16 (M+H)+.

Workup

  1. customit was purified on prep HPLC

Sources & evidence

ORD record
ord-d7648a7a15f74e65b3e397492c2ba528
Source dataset
uspto-grants-2010_05
Patent number
US07714138B2

Reaction notes

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