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

HRID 50039
Notes
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Reaction equation

HRID 50039 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 16212403L-Serinamide hydrochlorideHCID 213010464,5-Difluoro-3-(3,5-dimethylphenylsulphonyl)indole 2-carboxylic acid

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 min. 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-fe4a4dfcc1194e51bf3fffa66caf89b5
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06710068B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes