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

HRID 626543Notes

Reaction equation

HRID 626543 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:17])=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.Cl[C:26]([O:28][C:29]([CH3:31])=[CH2:30])=[O:27].O>N1C=CC=CC=1>[C:19]([NH:18][C:16](=[O:17])[NH:15][C:12]1[N:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:26](=[O:27])[O:28][C:29]([CH3:31])=[CH2:30])[CH:7]=2)=[CH:10][CH:11]=1)(=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 93846Isopropenyl chloroformateHCID 90409811N-((5-((2-aminopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide

Product 1

HCID 90445670Prop-1-en-2-yl (4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamateYield 54.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 0° C. suspension of Example C1 (1.2 g, 3.64 mmol) in pyridine (20 mL) was treated with isopropenyl chloroformate (0.398 mL, 3.64 mmol), stirred for 30 min, then treated with water. The resulting solid was collected via filtration and purified via silica gel chromatography (EtOAc/Hex, MeOH/DCM) to afford prop-1-en-2-yl (4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate (820 mg, 54%). MS (ESI) m/z: 414.2 (M+H+).

Workup

  1. filtrationThe resulting solid was collected via filtration
  2. custompurified via silica gel chromatography (EtOAc/Hex, MeOH/DCM)

Sources & evidence

ORD record
ord-e9b42f27212847df83233daa08bd2b54
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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