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Potassium Cyanide → 4-(6-cyano-5-(2,3-difluorobenzylamino)-1,2,4-triazin-3-ylamino)-N,N-dimethylbenzamide

HRID 577428
ノート
印刷プレビュー

反応式

HRID 577428 の反応式
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][C:3]=1[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[F:29].[C-:30]#[N:31].[K+].C1OCCOCCOCCOCCOCCOC1>CN1C(=O)CCC1>[C:30]([C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][C:3]=1[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[F:29])#[N:31]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 867064204-(6-chloro-5-(2,3-difluorobenzylamino)-1,2,4-triazin-3-ylamino)-N,N-dimethylbenzamide

生成物 1

HCID 867064214-(6-cyano-5-(2,3-difluorobenzylamino)-1,2,4-triazin-3-ylamino)-N,N-dimethylbenzamide

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
130 °C

実験手順

4-(6-Chloro-5-(2,3-difluorobenzylamino)-1,2,4-triazin-3-ylamino)-N,N-dimethylbenzamide (20 mg) was dissolved in 2 mL NMP. To it was added KCN (100 mg) and 18-crown-6 (20 mg). The mixture was stirred in a sealed tube at 130° C. for overnight. It was cooled to RT and subjected to reverse phase preparative HPLC to isolate the cyanation product, 4-(6-cyano-5-(2,3-difluorobenzylamino)-1,2,4-triazin-3-ylamino)-N,N-dimethylbenzamide. It was dissolved in 2 mL DMSO and 10 mL methanol. To it was added 100 mg KOH and then 1 mL H2O2 (50%). The mixture was stirred at RT for 1 h. It was treated with acetonitrile and TFA, concentrated and subjected to reverse phase preparative HPLC to isolate the title compound (3 mg). MS found for C20H19F2N7O2 as (M+H)+ 428.3. UV: λ=244, 278 nm. Proton NMR: (CD3OD) δ 7.53 (2H, d, J=8.8 Hz), 7.43 (2H, d, J=8.4 Hz), 7.20 (1H, m), 7.14-7.11 (2H, m), 4.84 (2H, s), 3.11 (3H, s), 3.04 (3H, s) ppm.

後処理

  1. temperatureIt was cooled to RT

出典と根拠

ORDレコード
ord-a49d3cdf11b64238b149152fde516790
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040530B2

反応ノート

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