Benzyl 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-5-fluoropyrimidin-4-yl)piperidin-4-ylcarbamate → 1-(4-(4-(4-(4-Aminopiperidin-1-yl)-5-fluoropyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

HRID 2381760Notes

Reaction equation

HRID 2381760 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:22]=[C:21]([N:23]4[CH2:28][CH2:27][CH:26]([NH:29]C(=O)OCC5C=CC=CC=5)[CH2:25][CH2:24]4)[C:20]([F:40])=[CH:19][N:18]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:29][CH:26]1[CH2:27][CH2:28][N:23]([C:21]2[C:20]([F:40])=[CH:19][N:18]=[C:17]([NH:16][C:13]3[CH:12]=[CH:11][C:10]([N:7]4[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]4)=[CH:15][CH:14]=3)[N:22]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 44467167Benzyl 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-5-fluoropyrimidin-4-yl)piperidin-4-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 444671681-(4-(4-(4-(4-Aminopiperidin-1-yl)-5-fluoropyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanoneYield 85.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-5-fluoropyrimidin-4-yl)piperidin-4-ylcarbamate (370 mg, 0.676 mmol) and Pd—C (10%, 55 mg) in MeOH (12 mL) was hydrogenated under balloon hydrogen for 20 h. It was then filtered through celite. The filtrate was concentrated in vacuo to give the titled compound (239 mg). MS 414.3 (M+H); UV 202.8, 268.8 nm.

Workup

  1. filtrationIt was then filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-edc3aef9225b45d699a476ad4bc39d44
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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