Methanol → HCID 178474871, compound

HRID 1373137Notes

Reaction equation

HRID 1373137 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N:13](C(=O)C)[S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:10][CH:11]=2)[C:6](=[C:26](OCC)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:5]1=[O:36])(=O)C.[C:37]([N:40]([C:50]1[CH:56]=[CH:55][C:53]([NH2:54])=[CH:52][CH:51]=1)[CH2:41][CH2:42][NH:43]C(=O)C(F)(F)F)(=[O:39])[CH3:38].CO.[OH-].[Na+]>CN(C=O)C.O>[C:37]([N:40]([C:50]1[CH:51]=[CH:52][C:53]([NH:54]/[C:26](=[C:6]2\[C:5](=[O:36])[NH:4][C:12]3[C:7]\2=[CH:8][C:9]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:10][CH:11]=3)/[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:55][CH:56]=1)[CH2:41][CH2:42][NH2:43])(=[O:39])[CH3:38]

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 120470014-[N-acetyl-N-(2-trifluoroacetylamino-ethyl)-amino]-anilineHCID 69509829HCID 69509829, compound

Product 1

HCID 178474871HCID 178474871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g (1 mmol) of 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-(N-acetyl-N-phenylsulphonyl-amino)-2-indolinone and 0.3 g (1.2 mmol) of 4-[N-acetyl-N-(2-trifluoroacetylamino-ethyl)-amino]-aniline are stirred in 5 ml of DMF for 6 hours at 120° C. After cooling to ambient temperature 5 ml of methanol and 3 ml (6 mmol) of 2 N sodium hydroxide solution are added, and the mixture is stirred for 30 minutes. The reaction mixture is diluted with 50 ml of water and the crystalline precipitate is suction filtered and dried. The residue is chromatographed on silica gel (dichloromethane/methanol/ammonia=9:1:0.1).

Workup

  1. additionare added
  2. filtrationfiltered
  3. customdried
  4. customThe residue is chromatographed on silica gel (dichloromethane/methanol/ammonia=9:1:0.1)

Sources & evidence

ORD record
ord-d7577033038f420bb8ac47a0ca3e5739
Source dataset
uspto-grants-2007_01
Patent number
US07160901B2

Reaction notes

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