HCID 10490410, compound → HCID 86610923, compound

HRID 1158781Notes

Reaction equation

HRID 1158781 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:15]([OH:17])=O)=[CH:5][N:4]=1.[CH2:19]([O:26][C:27]1[CH:28]=[C:29]([CH:33]([OH:39])[CH2:34][NH:35][CH2:36][CH2:37][OH:38])[CH:30]=[CH:31][CH:32]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([O:26][C:27]1[CH:28]=[C:29]([CH:33]([OH:39])[CH2:34][N:35]([CH2:36][CH2:37][OH:38])[C:15]([C:6]2[C:7]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[N:8][C:3]([N:2]([CH3:1])[CH3:18])=[N:4][CH:5]=2)=[O:17])[CH:30]=[CH:31][CH:32]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 10490410HCID 10490410, compoundHCID 68644616HCID 68644616, compound

Product 1

HCID 86610923HCID 86610923, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To activated 2-dimethylamino-4-phenylpyrimidine-5-carboxylic acid (1.48 g, 1 mmol/g, 1.48 mmol) bound to PS-TFP resin, N,N-dimethylformamide (20 ml), then after 5 minutes of swelling 1-(3-benzyloxyphenyl)-2-(2-hydroxyethylamino)ethanol (0.40 g, 1.39 mmol) is added. The reaction mixture is stirred at room temperature for 18 hours, then filtered and washed consecutively with 50-50 ml of NAN-dimethylformamide, tetrahydrofuran and dichloromethane. After evaporation the resulting oil (0.36 g) is chromatographed on silicagel using chloroform, and chloroform-ethyl acetate 9:1, 4:1 mixtures as eluents. 0.21 g of the title amide is obtained as white solid material, m.p. 89° C.

Workup

  1. filtrationfiltered
  2. washwashed consecutively with 50-50 ml of NAN-dimethylformamide, tetrahydrofuran and dichloromethane
  3. customAfter evaporation the resulting oil (0.36 g)
  4. customis chromatographed on silicagel

Sources & evidence

ORD record
ord-8ebc7d1e917d4a38908327ce19233940
Source dataset
uspto-grants-2010_10
Patent number
US07812031B2

Reaction notes

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