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

HRID 422036Notes

Reaction equation

HRID 422036 reaction equation
NC1C=C(C=CC=1)O[C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][C:11](=[O:15])[NH:12]2)=[CH:8][CH:7]=1.Cl.C[N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=2)[C:30]([OH:32])=O)[CH2:23]C1.C([N:43](CC)[CH:44]([CH3:46])[CH3:45])(C)C.CN(C(O[N:57]1N=N[C:59]2[CH:60]=CC=N[C:58]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:73]N(C=O)C>CCOC(C)=O>[CH3:73][C:26]1[N:21]=[CH:23][N:24]([C:27]2[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:35]=2)[C:30]([NH:57][C:58]2[CH:59]=[CH:60][CH:45]=[C:44]([NH:43][C:6]3[CH:14]=[C:13]4[C:9]([CH2:10][C:11](=[O:15])[NH:12]4)=[CH:8][CH:7]=3)[CH:46]=2)=[O:32])[CH:25]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 467382893-(4-Methyl-piperazin-1-yl)-5-trifluoromethyl-benzoic acid hydrochlorideHCID 598043186-(3-Amino-phenoxy)-1,3-dihydro-indol-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 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(3-amino-phenoxy)-1,3-dihydro-indol-2-one (200 mg, 0.83 mmol) and 3-(4-methyl-piperazin-1-yl)-5-trifluoromethyl-benzoic acid hydrochloride (291 mg, 0.89 mmol) in DMF (10 mL) is added N,N-diisopropylethylamine (164 μL, 1 mmol) followed by addition of HATU (380 mg, 1 mmol). The mixture is stirred at ambient temperature overnight. The mixture is diluted with EtOAc and washed with 10% aq Na2S2O3 solution and brine. The organic layer is separated, dried over MgSO4, and concentrated. The crude (310 mg) was used in the next step without further purification. LC/MS: 511.2 (MH+).

Workup

  1. washwashed with 10% aq Na2S2O3 solution and brine
  2. customThe organic layer is separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude (310 mg) was used in the next step without further purification

Sources & evidence

ORD record
ord-9145b9933c9048a0b6eb2985d70b8338
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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