Benzylamine → 2-[4-[[(Z)-[5-(benzenesulfonamido)-2-oxo-1H-indol-3-ylidene]-phenylmethyl]amino]phenyl]-N-benzylacetamide

HRID 989408Notes

Reaction equation

HRID 989408 reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]/[C:12](=[C:19]2\[C:20](=[O:38])[NH:21][C:22]3[C:27]\2=[CH:26][C:25]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:24][CH:23]=3)/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(O)=[O:2].[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C.O>[CH2:39]([NH:46][C:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11]/[C:12](=[C:19]2\[C:20](=[O:38])[NH:21][C:22]3[C:27]\2=[CH:26][C:25]([NH:28][S:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])=[CH:24][CH:23]=3)/[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:9][CH:10]=1)=[O:2])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178525187HCID 178525187, compound

Product 1

HCID 1785202942-[4-[[(Z)-[5-(benzenesulfonamido)-2-oxo-1H-indol-3-ylidene]-phenylmethyl]amino]phenyl]-N-benzylacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 315 mg (0.6 mmol) of (Z)-3-[1-(4-carboxymethyl-phenylamino)-1-phenyl-methylidene]-5-phenylsulphonylamino-2-indolinone, 85 mg (0.8 mmol) of benzylamine, 212 mg (0.66 mmol) of TBTU and 1 ml of N-ethyl-N,N-diisopropyl-amine in 5 ml of DMF is stirred for 3 hours at ambient temperature. Then 50 ml of water are added. The yellow precipitate formed is suction filtered, washed with water, a little isopropanol and ether, then dried in vacuo.

Workup

  1. customThe yellow precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. dry with materiala little isopropanol and ether, then dried in vacuo

Sources & evidence

ORD record
ord-53761e58622a4651817d1becc0812d54
Source dataset
uspto-grants-2003_10
Patent number
US06638965B2

Reaction notes

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