Sodium Iodide → HCID 14970438, compound

HRID 1034173Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([CH2:20][CH2:21][CH2:22][CH2:23]Cl)(=[O:19])=[O:18])[C:9]([N+:25]([O-:27])=[O:26])=[C:8]([CH3:28])[NH:7][C:6]=1[NH2:29])=[O:4].[I-].[Na+].[C:32](=[O:35])(O)[O-].[Na+].[CH3:37][N:38]([CH:40]=O)[CH3:39]>>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([CH2:20][CH2:21][CH2:22][CH2:23][N:7]2[CH2:8][CH2:40][N:38]([C:39]3[CH:12]=[CH:11][CH:10]=[CH:5][C:3]=3[O:35][CH3:32])[CH2:37][CH2:6]2)(=[O:19])=[O:18])[C:9]([N+:25]([O-:27])=[O:26])=[C:8]([CH3:28])[NH:7][C:6]=1[NH2:29])=[O:4]

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 6228Dimethylformamide

HCID 516892Sodium Bicarbonate

HCID 70074918HCID 70074918, compound

Product 1

HCID 14970438HCID 14970438, compound

Procedure

0.89 g of 2-amino-1,4-dihydro-4-{2-[(4-chlorobutyl)sulfonyl]phenyl}-6-methyl-5-nitro-3-pyridinecarboxylic acid methyl ester was treated with 0.60 g of sodium iodide, 0.34 g of sodium bicarbonate and 0.42 g of 2-methoxyphenyl-1-piperazine in 25 ml of DMF using the procedure as described for Example 3. Purification via column chromatography on silica gel, eluting with 60:35:5 toluene:ethyl acetate:methanol gave 0.10 g of product, m.p. 145°-147° C. 1H-NMR (d6 -DMSO) δ 1.57-1.63(m,2H); 1.80-1.87(m,2H); 2.36(t,2H,J=7 Hz); 2.45(s,3H); 2.49(s,4H); 2.94(s,4H); 3.35(m,2H); 3.40(s,3H); 3.77(s,3H); 6.50(s,1H); 6.88-6.92(m,6H); 7.35-7.81(m,4H); 9.50(br s,1H). Mass spectrum: 600 (M+H).

Workup

customPurification via column chromatography on silica gel
washeluting with 60:35:5 toluene

Sources & evidence

ORD record: ord-b10ac86408294987a29c25818c444bd6
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05314887

Reaction notes

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