Aniline → HCID 19704963, compound

HRID 727273Notes

Reaction equation

HRID 727273 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[CH:10]([CH2:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])[N:9]=2)=[CH:4][CH:3]=1.O[N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.NC1C=CC=CC=1>O.C(N(CC)CC)C.CN(C)C=O>[C:36]1([NH:32][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:14]3[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]23)[CH:37]=[CH:38][CH:39]=[CH:40][CH:35]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19705016HCID 19705016, compound

Product 1

HCID 19704963HCID 19704963, compoundYield 80.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

(±)-5-(4-(4-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)valeric acid (0.50 g) and 1-hydroxybenzotriazole (0.17 g) are added to dry dimethylformamide (20 ml) and the mixture is stirred under ice-cooling. Thereto is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.24 g), and then triethylamine (0.23 g) and aniline (0.10 g) are added. The mixture is stirred at room temperature for 4 days. After the completion of the reaction, water (100 ml) is added and the mixture is extracted with ethyl acetate. The organic layer is washed with 6N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate:methanol=10:l) and crystallized from ethyl acetate and isopropyl ether to give 0.47 g of (±)-N-phenyl-5-(4-(4-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepin-6-yl)pentaneamide as white powdery crystals, melting point 238°-240° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature for 4 days
  3. additionis added
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe organic layer is washed with 6N hydrochloric acid
  6. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (ethyl acetate:methanol=10:l)
  9. customcrystallized from ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-5549dcbc93394eba911f4e59b9757f47
Source dataset
uspto-grants-1998_01
Patent number
US05712274

Reaction notes

Loading…