Dimethylformamide → Carbamic acid, N-[3-[2-[3-[(5-cyano-2-pyrazinyl)amino]-1H-pyrazol-5-yl]-3-methoxyphenoxy]propyl]-, 1,1-dimethylethyl ester

HRID 1878313ノート

反応式

HRID 1878313 の反応式
Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9]2[CH:13]=[C:12]([C:14]3[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:15]=3[O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[NH:11][N:10]=2)=[N:6][CH:7]=1.[CH3:34][N:35](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:34]([C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9]2[CH:13]=[C:12]([C:14]3[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:15]=3[O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[NH:11][N:10]=2)=[N:6][CH:7]=1)#[N:35]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 86654391tert-Butyl 3-(2-(3-(5-bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenoxy)propylcarbamate

生成物 1

HCID 67232993Carbamic acid, N-[3-[2-[3-[(5-cyano-2-pyrazinyl)amino]-1H-pyrazol-5-yl]-3-methoxyphenoxy]propyl]-, 1,1-dimethylethyl ester収率 73%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
80 °C

実験手順

A solution of tert-butyl 3-(2-(3-(5-bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenoxy)propylcarbamate (0.378 g, 0.730 mmol) and zinc cyanide (0.10 g, 0.870 mmol) in DMF (10 mL) is degassed with a stream of nitrogen for one hour and then heated to 80° C. To the reaction is added Pd(Ph3P)4 (0.080 g, 0.070 mmol), and the mixture is heated overnight. The reaction is cooled to room temperature and concentrated under reduced pressure. The residue is purified by silica gel chromatography (CH2Cl2/MeOH) to give 0.251 g (73%) of the title compound.

後処理

  1. temperaturethe mixture is heated overnight
  2. temperatureThe reaction is cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by silica gel chromatography (CH2Cl2/MeOH)

出典と根拠

ORDレコード
ord-337364f942954eac94df49e81dd8665c
出典データセット
uspto-grants-2012_11
特許番号
US08314108B2

反応ノート

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