Dansyl chloride → HCID 178482652, compound

HRID 1383447Notes

Reaction equation

HRID 1383447 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]C=[C:16]3[C:11]=2C=CC=[N:15]3)=[CH:4][CH:3]=1.[S:25](Cl)([C:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[C:33]([N:34]([CH3:36])[CH3:35])[C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26]>N1C=CC=CC=1.C(OCC)(=O)C>[C:21]([N:20]=[C:8]([NH:9][C:10]1[CH:11]=[CH:16][N:15]=[CH:18][CH:19]=1)[NH:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:25]([C:28]2[C:40]3[C:32](=[C:33]([N:34]([CH3:36])[CH3:35])[CH:37]=[CH:38][CH:39]=3)[CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[CH:24][CH:23]=1)#[N:22]

Participants

5

Reactant 2

HCID 11801Dansyl chlorideHCID 178512242HCID 178512242, compound

Product 1

HCID 178482652HCID 178482652, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Amino-benzyl)-N′-cyano-N″-quinolin-5-yl-guanidine (400 mg, 1.50 mmol) and dansyl chloride (405 mg, 1.50 mmol) were combined in pyridine (15 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 (80 mL) and washed with water (40 mL×3). The organic phase was dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give a solid product which was purified by HPLC (yield=60%). 1H NMR (DMSO-d6, ppm): 10.73 (s, 1H), 9.09 (bs, 1H), 8.57 (d, 2H), 8.44 (d, 2H), 8.36 (d, 1H), 8.21 (d, 1H), 7.61 (m, 3H), 7.50 (s, 2H), 7.27 (d, 1H), 7.17 (d, 2H), 7.03 (d, 2H), 4.38 (d, 2H).

Workup

  1. customAn exothermic reaction
  2. washwashed with water (40 mL×3)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customto give a solid product which
  6. customwas purified by HPLC (yield=60%)

Sources & evidence

ORD record
ord-38f9420680f94425bf02b42f23d9a84c
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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