Triethylamine → HCID 21301040, compound

HRID 50036Notes

Reaction equation

HRID 50036 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:38]([OH:40])=O)=[C:32]2[S:41]([C:44]1[CH:49]=[C:48]([CH3:50])[CH:47]=[C:46]([CH3:51])[CH:45]=1)(=[O:43])=[O:42].[CH3:52][N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.C(N(CC)CC)C>CN(C=O)C.O>[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:38]([N:56]1[CH2:57][CH2:58][N:53]([CH3:52])[CH2:54][CH2:55]1)=[O:40])=[C:32]2[S:41]([C:44]1[CH:45]=[C:46]([CH3:51])[CH:47]=[C:48]([CH3:50])[CH:49]=1)(=[O:42])=[O:43]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 113719555-Chloro-3-(3,5-dimethylphenylsulfonyl)indole-2-carboxylic acid

Product 1

HCID 21301040HCID 21301040, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) (1.22 g, 0.00275 g) was added to a solution of 5-chloro-3-(3,5-dimethylphenyl-sulfonyl)indole-2-carboxylic acid (12) (1.00 g, 0.00275 mol), N-methylpiperazine (0.55 g, 0.0055 mol), triethylamine (0.55 g, 0.0055 mol) in anhydrous DMF (50 mL). Reaction was stirred at room temperature for 72 hours, then diluted with water and extracted with ethyl acetate. Organic extracts were washed with brine, dried and the solvent evaporated to give 1.20 g (98%) of pure title compound, mp 281-283° C. (from aqueous ethanol).

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate
  3. washOrganic extracts were washed with brine
  4. customdried
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-7f84c02c847e4154a40e74c72577487d
Source dataset
uspto-grants-2004_03
Patent number
US06710068B2

Reaction notes

Loading…