Diisopropylethylamine → 3-(4-methyl-imidazol-1-yl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-6-ylamino)-phenyl]-5-trifluoromethyl-benzamide

HRID 422005Notes

Reaction equation

HRID 422005 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][C:14](=[O:18])[NH:15]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:19][C:20]1[N:21]=[CH:22][N:23]([C:25]2[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=2)[C:28](O)=[O:29])[CH:24]=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.CCOC(C)=O>[CH3:19][C:20]1[N:21]=[CH:22][N:23]([C:25]2[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=2)[C:28]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]3[CH:17]=[C:16]4[C:12]([CH2:13][C:14](=[O:18])[NH:15]4)=[CH:11][CH:10]=3)[CH:3]=2)=[O:29])[CH:24]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 469002413-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acidHCID 593970496-((3-Aminophenyl)amino)indolin-2-one

Product 1

HCID 598043093-(4-methyl-imidazol-1-yl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-6-ylamino)-phenyl]-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(3-Amino-phenylamino)-1,3-dihydro-indol-2-one (36 mg, 0.15 mmol) and 3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoic acid (53 mg, 0.195 mmol) in DMF (1.5 mL) is added N,N-diisopropylethylamine (78 μL, 0.45 mmol) followed by addition of HATU (63 mg, 0.165 mmol). The mixture is stirred at ambient temperature overnight. The mixture is diluted with EtOAc and washed with 10% Na2S2O3 aqueous solution and brine. The organic layer is separated, dried over MgSO4, and concentrated. The crude product is used in the next step without further purification: LC-MS: 492.1 (MH+).

Workup

  1. washwashed with 10% Na2S2O3 aqueous solution and brine
  2. customThe organic layer is separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product is used in the next step without further purification

Sources & evidence

ORD record
ord-175d29bce9554219b4a2cade2a350a2c
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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