Water → (S)-N-(4-aminophenyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4, 3-a][1,4]diazepine-6-acetamide

HRID 727264Notes

Reaction equation

HRID 727264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@H:10]([CH2:24][C:25](O)=[O:26])[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:35]1[C:40]([NH2:41])=[CH:39][CH:38]=[C:37]([NH2:42])[CH:36]=1.O>CN(C)C=O>[NH2:41][C:40]1[CH:35]=[CH:36][C:37]([NH:42][C:25](=[O:26])[CH2:24][C@@H: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[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]23)=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7814P-PhenylenediamineHCID 8471TriethylamineHCID 668281072-((9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo(8.3.0.0,2,6)trideca-2(6),4,7,10,12-pentaen-9-yl)acetic acid

Product 1

HCID 68972164(S)-N-(4-aminophenyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4, 3-a][1,4]diazepine-6-acetamideYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (3.0 g), triethylamine (1.56 ml) and p-phenylenediamine (0.97 g) are dissolved in dimethylformamide (30 ml). Benzotriazol-1-yl-oxy-tris(dimethyl)phosphonium hexafluorophosphate (3.6 g) is added, and the mixture is stirred at room temperature for 12 hours. After the completion of the reaction, water (200 ml) is added, and the mixture is extracted with ethyl acetate. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. After the solvent is distilled away under reduced pressure, the residue is subjected to silica gel column chromatography and obtained crystals are recrystallized from toluene to give 0.56 g of (S)-N-(4-aminophenyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4, 3-a][1,4]diazepine-6-acetamide, melting point 169°-173° C.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent is distilled away under reduced pressure
  6. customobtained crystals
  7. customare recrystallized from toluene

Sources & evidence

ORD record
ord-ead28fc17d244738af9fd38d986aa4a3
Source dataset
uspto-grants-1998_01
Patent number
US05712274

Reaction notes

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