Water → HCID 11849164, compound

HRID 1640681Notes

Reaction equation

HRID 1640681 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:18]=2[NH:17][CH2:16][CH2:15]3)=[O:9])=[CH:4][CH:3]=1.Cl[C:20]1[N:25]=[C:24]([NH:26][C:27]2[CH:28]=[N:29][C:30]3[C:35]([CH:36]=2)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:23]=[CH:22][N:21]=1.C(OCC)(=O)C.O>CS(C)=O>[NH:17]1[C:18]2[C:14](=[CH:13][CH:12]=[CH:11][C:10]=2[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:20]3[N:25]=[C:24]([NH:26][C:27]4[CH:28]=[N:29][C:30]5[C:35]([CH:36]=4)=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:23]=[CH:22][N:21]=3)=[CH:7][CH:6]=2)=[O:9])[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 22326846(2-Chloropyrimidin-4-yl)quinolin-3-ylamineHCID 66737937HCID 66737937, compound

Product 1

HCID 11849164HCID 11849164, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

200 mg (0.84 mmol) of (4-aminophenyl)-(2,3-dihydro-1H-indol-7-yl)methanone and 215 mg (0.84 mmol) of (2-chloropyrimidin-4-yl)quinolin-3-ylamine are warmed at 120° C. for 2 h in 2 ml of DMSO. The organic phase is stirred with ethyl acetate and water and purified by chromatography over silica gel after phase separation, drying and evaporation, giving 500 mg of (2,3-di-hydro-1H-indol-7-yl)-{4-[4-(quinolin-3ylaminopyrimidin-2-ylamino]phenyl}-methanone. (M.p.: 235-238° C.)

Workup

  1. custompurified by chromatography over silica gel
  2. customafter phase separation
  3. customdrying
  4. customevaporation
  5. customgiving 500 mg of (2,3-di-hydro-1H-indol-7-yl)-{4-[4-(quinolin-3ylaminopyrimidin-2-ylamino]phenyl}-methanone

Sources & evidence

ORD record
ord-2f259831f1c84daca9f207ffa40d38ac
Source dataset
uspto-grants-2012_02
Patent number
US08114882B2

Reaction notes

Loading…