Water → 4-(2-(4-(4-Acetylpiperazin-1-yl)phenylamino)-5-fluoropyrimidin-4-yl)piperazine-1-carboxamide

HRID 2281531Notes

Reaction equation

[F:1][C:2]1[C:3]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[C-:30]#[N:31].[K+].[OH2:33]>CC#N>[C:21]([N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:5]3[N:4]=[C:3]([N:24]4[CH2:29][CH2:28][N:27]([C:30]([NH2:31])=[O:33])[CH2:26][CH2:25]4)[C:2]([F:1])=[CH:7][N:6]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1)(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 1-(4-(4-(5-fluoro-4-(piperazin-1-yl)pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (53 mg, 0.13 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 stirred at 70° C. for 3 h. It was then purified by HPLC to give the titled compound (15 mg). MS 443.3 (M+H); UV 201.8, 269.8 nm.

Workup

customIt was then purified by HPLC

Sources & evidence

ORD record: ord-949412e89909450f936c8e713af55e2b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139581B2

Reaction notes

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