Dimethylformamide → 4,5-Difluoro-3-(3,5-dimethylphenylsulphonyl) indole 2-carboxyserinamide

HRID 902176Notes

Reaction equation

HRID 902176 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([S:15]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=1)(=[O:17])=[O:16])=[C:5]([C:12](O)=[O:13])[NH:6]2.Cl.[NH2:27][C@H:28]([C:31]([NH2:33])=[O:32])[CH2:29][OH:30].C(N(CC)CC)C.CN(C)C=[O:44]>O>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([S:15]([C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1)(=[O:17])=[O:16])=[CH:5][NH:6]2.[C:29]([C@@:28]([C:31]([NH2:33])=[O:32])([CH2:12][OH:13])[NH2:27])([OH:44])=[O:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 16212403L-Serinamide hydrochlorideHCID 21301046HCID 21301046, compound

Product 1

HCID 690293034,5-Difluoro-3-(3,5-dimethylphenylsulphonyl) indole 2-carboxyserinamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,5-Difluoro-3-(3,5-dimethylphenylsulphonyl)indole 2-carboxylic acid (3.52 g) and L-serinamide hydrochloride (2.77 g) were dissolved in anhydrous dimethylformamide (90 ml). Triethylamine (2.8 ml) was added and the mixture stirred for 5 minutes. Benzotriazol-1-yloxy-tris(dimethylamino)phosphosphonium hexafluorophosphate (BOP) (4.69 g) was added and the orange mixture was stirred overnight at room temperature. The reaction mixture was diluted with water (350 ml) and the white solid precipitate collected by filtration, washed with water and dried to afford the title product (3.86 g) as a white powder (97.9% pure by hplc).

Workup

  1. stirringthe orange mixture was stirred overnight at room temperature
  2. filtrationthe white solid precipitate collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d86e541ad6b84fa4905d7022efd896e1
Source dataset
uspto-grants-2008_04
Patent number
US07365090B2

Reaction notes

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