Dichloromethane → HCID 22674968, compound

HRID 1005767Notes

Reaction equation

HRID 1005767 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][N+:24]([O-:27])=[CH:23][CH:22]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36](O)=[O:37])[CH2:31][CH2:30]1.N1(C2C=CN=CC=2)CCCC1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)[Cl:66]>>[ClH:66].[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]([N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:19]=[CH:20]/[C:21]2[CH:22]=[CH:23][N+:24]([O-:27])=[CH:25][CH:26]=2)[S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])=[O:37])[CH2:31][CH2:30]1

Participants

6

Reactant 5

HCID 6344Dichloromethane2×HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 2762732(4-Methylpiperazin-1-yl)acetic acidHCID 178492875HCID 178492875, compound

Product 1

HCID 22674968HCID 22674968, compound

Procedure

(E) -4-(2-(2-(N-(4-Methoxybenzenesulfonyl)amino)phenyl)ethenyl) pyridine 1-oxide (0.96 g) was dissolved in methylene chloride (25 ml), and 4-methylpiperazin-1-yl acetic acid (0.99 g) prepared in Reference Example 1 and 4-pyrrolidinopyridine (37 mg) were added thereto. To the mixture was added dropwise N,N′-dicyclohexylcarbodiimide (1.29 g) dissolved in methylene chloride (13 ml), and the mixture was stirred over night at room temperature. The reaction solution was filtered and the filtrate was concentrated. The resultant residue was subjected to silica gel column chromatography (eluent: CHCl3/CH3OH=100/1 to 10/1) to obtain fractions. To each fraction was added hydrochloric acid-ether solution followed by concentration. The residue was diluted with water, filtered through membrane filter and lyophilized to yield the objective compound (1.25 g, colorless powder).

Workup

  1. additionwere added
  2. filtrationThe reaction solution was filtered
  3. concentrationthe filtrate was concentrated
  4. customto obtain fractions
  5. concentrationfollowed by concentration
  6. additionThe residue was diluted with water
  7. filtrationfiltered through membrane
  8. filtrationfilter
  9. customto yield the objective compound (1.25 g, colorless powder)

Sources & evidence

ORD record
ord-543df6746c534167a1217f5a4cd1336e
Source dataset
uspto-grants-2004_09
Patent number
US06787546B2

Reaction notes

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