Dichloromethane methanol → 5-(6-Amino-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid [4-(4-ethyl-piperazin-1-ylmethyl)-phenyl]-amide

HRID 2264588Notes

Reaction equation

HRID 2264588 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:19]3[C:27]4[C:22](=[CH:23][C:24]([O:28][C:29]5[CH:34]=[C:33]([N:35]=[N+]=[N-])[N:32]=[CH:31][N:30]=5)=[CH:25][CH:26]=4)[CH2:21][CH2:20]3)=[O:18])=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)[CH3:2].C(Cl)Cl.CO>C1COCC1.[Pd]>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:19]3[C:27]4[C:22](=[CH:23][C:24]([O:28][C:29]5[CH:34]=[C:33]([NH2:35])[N:32]=[CH:31][N:30]=5)=[CH:25][CH:26]=4)[CH2:21][CH2:20]3)=[O:18])=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 595964065-(6-Azido-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid [4-(4-ethyl-piperazin-1-ylmethyl)-phenyl]-amide

Product 1

HCID 595963875-(6-Amino-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid [4-(4-ethyl-piperazin-1-ylmethyl)-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenation of 0.38 mMol 5-(6-azido-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid [4-(4-ethyl-piperazin-1-ylmethyl)-phenyl]-amide in 10 ml THF in the presence of 70 mg Pd/C 10%, filtration, concentration of the filtrate, chromatography (Combi Flash; CH2Cl2/MeOH/NH3conc. 98:2:0→90:10:1) and crystallization from DIPE gives the title compound: MS: [M+1]+=474; TLC(EtOAc/EtOH/NH3conc. 80:20:1): Rf=0.09; Anal.: C,H,N.

Sources & evidence

ORD record
ord-a56f4f0c7a93462fb0ac318ae5986651
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

Loading…