Pyridine → HCID 178512315, compound

HRID 1383446Notes

Reaction equation

HRID 1383446 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([NH:20][C:21]#[N:22])=[N:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[N:15]3)=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.N1C=CC=CC=1>C(OCC)(=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([NH:9][C:10]3[CH:19]=[CH:18][CH:17]=[C:16]4[C:11]=3[CH:12]=[CH:13][CH:14]=[N:15]4)=[N:20][C:21]#[N:22])=[CH:23][CH:24]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 178512242HCID 178512242, compound

Product 1

HCID 178512315HCID 178512315, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Amino-benzyl)-N′-cyano-N″-quinolin-5-yl-guanidine (50 mg, 0.16 mmol) and 4-chloro-benzenesulfonyl chloride (41 mg, 0.19 mmol) were added to pyridine (1 mL). An exothermic reaction occurred and the suspension became homogeneous. This solution was shaken at room temperature for 12 hours. The reaction mixture was then diluted with ethyl acetate (8 mL) and washed with water (5 mL×3). The organic phase was dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was triturated with diethyl ether to give a solid product in 76% yield. 1H NMR (DMSO-d6, ppm): 10.37 (s, 1H), 9.39 (s, 1H), 8.96 (m, 1H), 8.12 (m, 1H), 8.02 (d, 1H), 7.69 (m, 3H), 7.63 (d, 2H), 7.49 (m, 2H), 7.39 (m, 1H), 7.08 (m, 4H), 4.21 (d, 2H).

Workup

  1. customAn exothermic reaction
  2. washwashed with water (5 mL×3)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was triturated with diethyl ether
  6. customto give a solid product in 76% yield

Sources & evidence

ORD record
ord-ee6881d7cc2f4449ac9da3101cbb9e11
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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