Water → 1-(1-(2-(4-(4-Acetylpiperazin-1-yl)phenylamino)-5-fluoropyrimidin-4-yl)piperidin-4-yl)urea

HRID 2381761Notes

Reaction equation

HRID 2381761 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([F:14])=[CH:12][N:11]=[C:10]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:9]=2)[CH2:4][CH2:3]1.[C-:31]#[N:32].[K+].[OH2:34]>CC#N>[C:28]([N:25]1[CH2:26][CH2:27][N:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:10]3[N:9]=[C:8]([N:5]4[CH2:6][CH2:7][CH:2]([NH:1][C:31]([NH2:32])=[O:34])[CH2:3][CH2:4]4)[C:13]([F:14])=[CH:12][N:11]=3)=[CH:21][CH:20]=2)[CH2:23][CH2:24]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 444671681-(4-(4-(4-(4-Aminopiperidin-1-yl)-5-fluoropyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

Product 1

HCID 444671691-(1-(2-(4-(4-Acetylpiperazin-1-yl)phenylamino)-5-fluoropyrimidin-4-yl)piperidin-4-yl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1-(4-(4-(4-(4-aminopiperidin-1-yl)-5-fluoropyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (48 mg, 0.12 mmol) in CH3CN (2 mL), a solution of KCN (60 mg, 0.74 mmol) in H2O (2 mL) was added. The suspension became clear. The mixture was stiffed at 70° C. for 2 h. It was then purified by HPLC to give the titled compound (12 mg). MS 457.3 (M+H); UV 204.8, 266.8 nm.

Workup

  1. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-68ea88efe243406a96de862834634f2e
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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