Dimethylformamide → HCID 67197922, compound

HRID 545532Notes

Reaction equation

HRID 545532 reaction equation
Br[CH:2]([CH3:6])[C:3](=O)C.[F:7][C:8]1[CH:9]=[C:10]([CH:34]=[CH:35][CH:36]=1)[CH2:11][N:12]1[C:24]2[CH2:23][CH2:22][C@@H:21]([NH:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[CH2:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[C:16]([C:31](=[S:33])[NH2:32])[CH:17]=2.[CH3:37]N(C=O)C>O>[F:7][C:8]1[CH:9]=[C:10]([CH:34]=[CH:35][CH:36]=1)[CH2:11][N:12]1[C:24]2[CH2:23][CH2:22][C@@H:21]([NH:25][C:26](=[O:30])[CH:27]([CH3:28])[CH3:29])[CH2:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[C:16]([CH:31]1[N:32]([CH3:37])[C:2]([CH3:6])=[CH:3][S:33]1)[CH:17]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 131422-Butanone, 3-bromo-HCID 59161227HCID 59161227, compound

Product 1

HCID 67197922HCID 67197922, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 3-bromo-2-butanone (0.224 g, 1.48 mmol) and (R)-N-(9-(3-fluorobenzyl)-6-thiocarbamoyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Preparation 22) (0.209 g, 0.493 mmol) and heat in DMF at 80° C. under nitrogen for 2 h. Upon cooling, dilute the mixture with water and collect the precipitate by filtration. Recrystallize from absolute EtOH to give yellow crystals: MS (ES): m/z 476 (M+1); HPLC: Rt=3.87 min (100%).

Workup

  1. temperatureUpon cooling
  2. customcollect the precipitate
  3. filtrationby filtration
  4. customRecrystallize from absolute EtOH
  5. customto give yellow crystals

Sources & evidence

ORD record
ord-2b432992fe9c4f4ab4b822162efa9afb
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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