Water → HCID 59596388, compound

HRID 2264594Notes

Reaction equation

HRID 2264594 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH2:14][CH2:13]3)[CH:4]=1.[C:19]([C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].CCOC(C)=O.O>C1COCC1>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([N:15]2[C:16]3[C:12](=[CH:11][C:10]([O:9][C:5]4[CH:4]=[C:3]([NH:2][CH3:1])[N:8]=[CH:7][N:6]=4)=[CH:18][CH:17]=3)[CH2:13][CH2:14]2)=[O:31])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 67531579HCID 67531579, compound

Product 1

HCID 59596388HCID 59596388, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 70 mg (0.3 mMol) 5-(6-methylamino-pyrimidin-4-yloxy)-2,3-dihydro-indole (Step 21.2) and 70 mg (0.4 mMol) 4-tert.butyl-phenylisocyanat in 2 ml THF is stirred for 75 min at rt. The reaction mixture is dissolved with EtOAc and water, the aqueous layer separated off and extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; EtOAc/hexane 1:1→3:1→4:1) gives the title compound: MS: [M+1]+=418; TLC(EtOAc): Rf=0.20.

Workup

  1. customthe aqueous layer separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-68b26c1447364f159df5325604a29153
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

Loading…