Dimethylformamide → RS-93522

HRID 652550Notes

Reaction equation

HRID 652550 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:33])=[C:5]([C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].Br[CH2:35][CH2:36][OH:37].C(N(CC)CC)C.CN([CH:48]=[O:49])C>O>[CH3:1][C:2]1[NH:3][C:4]([CH3:33])=[C:5]([C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:35][CH:36]([OH:37])[CH2:48][OH:49])=[CH:30][CH:31]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 108982-BromoethanolHCID 201974812,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridine

Product 1

HCID 128487RS-93522

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Similarly, a solution of 4.5 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-aminophenyl)ethoxycarbonyl]-1,4-dihydropyridine (11), 1.8 mL 2-bromoethanol, 2 mL triethylamine and 20 mL DMF was stirred at 80° C. for 3 h. The mixture was added to water and extracted with ethyl acetate. The ethyl acetate was washed with water, dried over Na2SO4, evaporated to a residue, and purified by silica gel chromatography with 75% ethyl acetate-hexane to afford 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethylamino)phenyl]ethoxycarbonyl)-1,4-dihydropyridine (1) as a free base. This was dissolved in methanolic HCl and evaporated under reduced pressure to yield 2.6 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethylamino)phenyl]ethoxycarbonyl)-1,4-dihydropyridine hydrochloride as an amorphous solid, m.p. 102°-104° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated to a residue
  5. custompurified by silica gel chromatography with 75% ethyl acetate-hexane

Sources & evidence

ORD record
ord-5021a2f6cc1041cd80ae373014506b72
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

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