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

HRID 1878313Notes

Reaction equation

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]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-337364f942954eac94df49e81dd8665c
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314108B2

Reaction notes

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