1-Amino-3-[methyl(phenyl)amino]propan-2-ol → 5-[4-{2-[3-(N-Methyl-N-phenylamino)-2-hydroxypropylamino]propoxy}benzyl]thiazolidine-2,4-dione

HRID 2294289Notes

Reaction equation

HRID 2294289 reaction equation
[CH3:1][N:2]([CH2:9][CH:10]([OH:13])[CH2:11][NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O=[C:15]([CH3:32])[CH2:16][O:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][CH:23]2[S:27][C:26](=[O:28])[NH:25][C:24]2=[O:29])=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>CO>[CH3:1][N:2]([CH2:9][CH:10]([OH:13])[CH2:11][NH:12][CH:15]([CH3:32])[CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][CH:23]2[S:27][C:26](=[O:28])[NH:25][C:24]2=[O:29])=[CH:30][CH:31]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 2725791-Amino-3-[methyl(phenyl)amino]propan-2-olHCID 5003444Sodium cyanoborohydrideHCID 218321505-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 214747085-[4-{2-[3-(N-Methyl-N-phenylamino)-2-hydroxypropylamino]propoxy}benzyl]thiazolidine-2,4-dioneYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Example 2 was repeated, except that 1.55 g of 3-(N-methyl-N-phenylamino)-2-hydroxypropylamine (prepared as described in Preparation 90), 1.6 g of 5-[4-(2-oxopropoxy)benzyl]-thiazolidine-2,4-dione, 0.4 g of sodium cyanoborohydride and 50 ml of anhydrous methanol were used, to give 1.39 g of the title compound, melting at 115° C. to 125° C.

Sources & evidence

ORD record
ord-a0cb3737e26d4ea5b6ab85cb89c6d14f
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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