Water → HCID 86678333, compound

HRID 1402581Notes

Reaction equation

HRID 1402581 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[CH:31]=4)=[O:28])=[CH:22][CH:21]=3)[CH:16]=[CH:15][N:14]=2)[NH:10][CH:9]=1)=[O:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:36][C:32]1[CH:31]=[C:30]([NH:29][C:27]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][C:17]3[CH:16]=[CH:15][N:14]=[C:13]([C:11]4[NH:10][CH:9]=[C:8]([C:6]([NH:5][CH2:4][CH2:3][CH:2]=[O:1])=[O:7])[CH:12]=4)[CH:18]=3)=[CH:21][CH:22]=2)=[O:28])[CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 71293502HCID 71293502, compound

Product 1

HCID 86678333HCID 86678333, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(3-hydroxypropyl)-5-{4-[4-({[(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamide (1.0 g, 2.06 mmol) in 20 ml of anhydrous DMF was added Dess-Martin periodinane (1.22 g, 2.88 mmol). The mixture was stirred at room temperature under nitrogen for 80 minutes and poured into 100 ml of water with vigorous stirring. Saturated NaHCO3 solution was added until pH=9. The precipitates were filtered, washed with water and dried in vacuo to give the crude 5-{4-[4-({[(3-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-N-(3-oxopropyl)-1H-pyrrole-3-carboxamide as light brown solid, which was used in the next step without further purification. Yield: 1.0 g, 100%.

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e98adf6ea1ce4b87970331ab4d4bd7f7
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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