2-Propoxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-{[(propan-2-yl)sulfamoyl]acetyl}-1,4-dihydropyridine-3-carboxylate → HCID 70416516, compound

HRID 1252262Notes

Reaction equation

HRID 1252262 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8](=[O:36])[C:9]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:13]([C:24](=O)[CH2:25][S:26](=[O:32])(=[O:31])[NH:27][CH:28]([CH3:30])[CH3:29])=[C:12]([CH3:34])[NH:11][C:10]=1[CH3:35])[CH2:2][CH3:3].[BH4-].[Na+].C(Cl)Cl.C(OCC)(=O)C>C(O)C.CN(C)C=O>[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8](=[O:36])[C:9]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:13](/[CH:24]=[CH:25]/[S:26](=[O:31])(=[O:32])[NH:27][CH:28]([CH3:30])[CH3:29])=[C:12]([CH3:34])[NH:11][C:10]=1[CH3:35])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 1282442-Propoxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-{[(propan-2-yl)sulfamoyl]acetyl}-1,4-dihydropyridine-3-carboxylateHCID 4311764Sodium borohydrideHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 70416516HCID 70416516, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

Analogously to Example 18, 1.05 g of 1,4-dihydro-5-[(isopropylsulfamoyl)acetyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2-propoxyethyl ester were treated with 0.08 g of sodium borohydride in a mixture of 10 ml of ethanol and 2 ml of dimethylformamide. After chromatography with methylene chloride/ethyl acetate (4:1) as the elution agent there was obtained 0.90 g of 1,4-dihydro-5-[(E)-2-(isopropylsulfamoyl)vinyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2-propoxyethyl ester in the form of yellow crystals, m.p. 152°-154°.

Sources & evidence

ORD record
ord-e2bf6b95184b4cb199981c020ce157f5
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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