Benzoyl chloride → HCID 71468850, compound

HRID 1401089Notes

Reaction equation

HRID 1401089 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([N:14]([CH:24]([CH3:26])[CH3:25])[NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])=[CH:2]1.CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O>[C:36]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([N:14]([CH:24]([CH3:26])[CH3:25])[NH:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:13])=[CH:2]1)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 71468594HCID 71468594, compound

Product 1

HCID 71468850HCID 71468850, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask, (E)-N′-(3-(1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide (50 mg, 0.14 mmol, 1.0 equivalent), and DMAP (cat, 4.0 mg, 0.14 equivalent) were introduced and dissolved in CH2Cl2, after which DIPEA (0.04 ml, 0.20 mmol, 1.5 equivalent) was introduced. After introducing benzoyl chloride (0.02 ml, 0.17 mmol, 1.2 equivalent) at 0° C. and stirring at room temperature for 24 hr, the reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc:=1:1) and dried so that solid form of (E)-N′-(3-(1-benzoyl-1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide was obtained. (48.0 mg, 77%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated through silica gel chromatography (n-hexane:EtOAc:=1:1)
  6. dry with materialdried so that solid form of (E)-N′-(3-(1-benzoyl-1H-indol-3-yl)acryloyl)-N′-isopropylbenzohydrazide
  7. customwas obtained

Sources & evidence

ORD record
ord-33cde847c0d3457aaf01ecba9b666ca7
Source dataset
uspto-grants-2014_12
Patent number
US08906952B2

Reaction notes

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