Ethyl Acetate → 6-(6-Methylamino-pyrimidin-4-yloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid (4-tert.butyl-phenyl)-amide

HRID 2264569Notes

Reaction equation

HRID 2264569 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:17](=[CH:18][CH:19]=2)[NH:16][CH2:15][CH2:14][CH2:13]3)[CH:4]=1.[C:20]([C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].CCCCCC.CCOC(C)=O.CCOC(C)=O>C1COCC1.CCOCC>[C:20]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([N:16]2[C:17]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:19][CH:18]=3)[CH2:13][CH2:14][CH2:15]2)=[O:32])=[CH:26][CH:25]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 21226206Ethyl acetate hexaneHCID 675311756-Methylamino-4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-pyrimidine

Product 1

HCID 117116996-(6-Methylamino-pyrimidin-4-yloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid (4-tert.butyl-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 90 mg (0.35 mMol) of 6-methylamino-4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-pyrimidine (Step 3.2) in 2 ml of THF and a solution of 63.3 mg (97%; 0-35 mMol) of 4-tert.butyl-phenyl-isocyanate in 4 ml ether are mixed and stirred for 30 min. After concentration of the reaction mixture, a chromatography (Combi Flash; hexane/EtOAc 1:2→EtOAc) gives the title compound: m.p.: 175-176° C.; MS: [M+1]+=432; Anal.: C,H,N.

Sources & evidence

ORD record
ord-d997dc7e4d0a439d809d3f59bd8cfa9e
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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