Water → Prop-1-en-2-yl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate

HRID 626573Notes

Reaction equation

HRID 626573 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:16][C:17]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:18])=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.Cl[C:27]([O:29][C:30]([CH3:32])=[CH2:31])=[O:28].O.C(Cl)Cl>N1C=CC=CC=1>[CH3:15][C:14]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:27](=[O:28])[O:29][C:30]([CH3:32])=[CH2:31])[CH:7]=2)=[CH:10][CH:11]=[C:12]([NH:16][C:17]([NH:19][C:20](=[O:25])[C:21]([CH3:22])([CH3:24])[CH3:23])=[O:18])[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 93846Isopropenyl chloroformateHCID 90410520N-((5-((2-aminopyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamide

Product 1

HCID 131735228Prop-1-en-2-yl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamateYield 94.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of N-((5-((2-aminopyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamide (0.280 g, 0.815 mmol) in pyridine (6 mL) was treated with isopropenyl chloroformate (0.100 mL, 0.913 mmol) and stirred at RT overnight. The mixture was treated with water and DCM, stirred for 0.5 h, the layers separated and the aqueous layer extracted with additional DCM (3×). The combined organics were dried over Na2SO4 and concentrated to dryness to afford prop-1-en-2-yl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate (328 mg, 94%). MS (ESI) m/z: 428.2 (M+H+).

Workup

  1. stirringstirred for 0.5 h
  2. customthe layers separated
  3. extractionthe aqueous layer extracted with additional DCM (3×)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2af0b87d70204ed78f6ec8cdb2f1b582
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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