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

HRID 2264589Notes

Reaction equation

HRID 2264589 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](Cl)[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].[CH3:36][NH2:37]>C1COCC1>[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]([NH:37][CH3:36])[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]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 11547733HCID 11547733, compound

Product 1

HCID 595963535-(6-Methylamino-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid [4-(4-ethyl-piperazin-1-ylmethyl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 134 mg (0.27 mMol) 5-(6-chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid [4-(4-ethyl-piperazin-1-ylmethyl)-phenyl]-amide in 5 ml THF and 1.2 ml methylamin solution (2 M in THF) is stirred for 3 d in a sealed tube at rt. The reaction mixture is concentrated and the residue chromatographed by reversed phase MPLC (Gilson system), yielding the title compound: MS: [M+1]+=488; HPLC: BtRet=11.5.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue chromatographed by reversed phase MPLC (Gilson system)

Sources & evidence

ORD record
ord-a66541ee38784db982019233881349a6
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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