Hydrochloric Acid → HCID 131722606, compound

HRID 1066348Notes

Reaction equation

HRID 1066348 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[C:19]([C:21](O)=O)[CH:18]=[CH:17][N:16]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:36]([S:41](N)(=[O:43])=[O:42])[CH2:37][CH2:38][CH2:39][CH3:40].N12CCCN=C1CCCCC2.Cl.C[N:58](C)[CH:59]=[O:60]>>[CH2:36]([S:41]([NH:58][C:59]([CH2:21][C:19]1[CH:18]=[CH:17][N:16]=[C:15](/[CH:14]=[CH:13]/[C:10]2[CH:11]=[CH:12][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=2)[CH:20]=1)=[O:60])(=[O:43])=[O:42])[CH2:37][CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109206961-PentanesulfonamideHCID 22388054HCID 22388054, compound

Product 1

HCID 131722606HCID 131722606, compound

Procedure

(E)-2-(2-(4-phenylphenyl)ethenyl)pyridine-4-carboxylic acid (277 mg) was dissolved in 2.8 ml of dried dimethylformamide, and 194 mg of carbonyldiimidazole was added thereto. The mixture was stirred at room temperature for 1.5 hours and then stirred at 100° C. for 30 minutes. After being cooled to room temperature, the mixture was mixed with 209 mg of pentanesulfonamide and 210 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene and stirred at 100° C. for 48 hours. The reaction mixture was cooled with ice, and then its pH was adjusted to 5 using 1N hydrochloric acid. The resulting precipitate was collected by filtration and washed with water. The partially purified material thus obtained was further purified by silica-gel thin-layer chromatography (eluent, chloroform:methanol:water=65:25:4) to yield 67 mg of brown powder of (E)-N-(n-pentanesulfonyl)-2-(2-(4-phenylphenyl)ethenyl)pyridine-4-carboxyamide.

Workup

  1. stirringstirred at 100° C. for 30 minutes
  2. temperatureAfter being cooled to room temperature
  3. stirringstirred at 100° C. for 48 hours
  4. temperatureThe reaction mixture was cooled with ice
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customThe partially purified material thus obtained
  8. customwas further purified by silica-gel thin-layer chromatography (eluent, chloroform:methanol:water=65:25:4)

Sources & evidence

ORD record
ord-ac09052c541b45ba9226ed5c7c960e9c
Source dataset
uspto-grants-2001_06
Patent number
US06242474B1

Reaction notes

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