Darglitazone → HCID 9845142, compound

HRID 654247Notes

Reaction equation

HRID 654247 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)=[O:16].[BH4-].[Na+]>C(O)(C)C>[C:7]1([C:5]2[O:6][C:2]([CH3:1])=[C:3]([CH2:13][CH2:14][CH:15]([C:17]3[CH:30]=[CH:29][C:20]([CH2:21][CH:22]4[S:26][C:25](=[O:27])[NH:24][C:23]4=[O:28])=[CH:19][CH:18]=3)[OH:16])[N:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 60870DarglitazoneHCID 4311764Sodium borohydride

Product 1

HCID 9845142HCID 9845142, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title product of Example 9 (0.70 g) was suspended in 50 ml of isopropanol at room temperature. NaBH4 (0.15 g) was added and the mixture stirred for 2 hours, concentrated in vacuo to low volume, diluted with 50 ml of water and extracted 2×200 mL ethyl acetate. The organic layers were combined, washed with brine, dried (MgSO4), stripped in vacuo and the residue chromatographed using 1:1 ethyl acetate:hexane-1% acetic acid to yield 0.32 g of present title product; mp 50°-55° C.; tlc Rf 0.40 (1:1 hexane:ethyl acetate-2.5% acetic acid), 0.28 (2:1 CH2Cl2 :ether).

Workup

  1. concentrationconcentrated in vacuo to low volume
  2. additiondiluted with 50 ml of water
  3. extractionextracted 2×200 mL ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customthe residue chromatographed

Sources & evidence

ORD record
ord-e27d91d6fe7e4d8b8c5b7fcea79d8b90
Source dataset
uspto-grants-1992_07
Patent number
US05130379

Reaction notes

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