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

HRID 1878313노트

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HRID 1878313 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-337364f942954eac94df49e81dd8665c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314108B2

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