Diisopropylethylamine → 4-(4-methyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-7-ylamino)-phenyl]-benzamide

HRID 422021Notes

Reaction equation

HRID 422021 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:17]=2[NH:16][C:15](=[O:18])[CH2:14]3)[CH:5]=[CH:6][CH:7]=1.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=2)[CH2:22][CH2:21]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:35]=[CH:34][C:30]([C:31]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[C:13]5[C:17]=4[NH:16][C:15](=[O:18])[CH2:14]5)[CH:3]=3)=[O:32])=[CH:29][CH:28]=2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 598042847-(3-Amino-phenylamino)-1,3-dihydro-indol-2-one

Product 1

HCID 598043654-(4-methyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-7-ylamino)-phenyl]-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(3-amino-phenylamino)-1,3-dihydro-indol-2-one (80 mg, 0.33 mmol) in DMF (2 ml) is added 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid (113 mg, 0.37 mmol), N,N-diisopropylethylamine (0.22 g, 1.67 mmol) and HATU (0.14 g, 0.37 mmol). The reaction is stirred for 12 hours and concentrated. The residue is purified by HPLC to afford the desired compound: LC-MS: 456.2 (MH+).

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-a8e84ea0c2614cdbb59812d71d3272a8
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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