Potassium Carbonate → HCID 9815137, compound

HRID 1355368Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[C:9]([C:18]#[N:19])=[N:10][CH:11]=[C:12]([NH:14][CH2:15][CH2:16][OH:17])[N:13]=1.Cl.[CH2:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][CH2:24][NH:23][CH2:22]1>CN(C)C=O>[OH:17][CH2:16][CH2:15][NH:14][C:12]1[N:13]=[C:8]([N:23]2[CH2:22][CH2:21][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[CH2:25][CH2:24]2)[C:9]([C:18]#[N:19])=[N:10][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.415 g (3.00 mmol) of potassium carbonate were added slowly at room temperature to a solution of 0.243 g (1.0 mmol) of the 3-bromo-5-(2-hydroxy-ethylamino)-pyrazine-2-carbonitrile and 0.220 g (1.2 mmol) of the 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride (J. Heterocycl. Chem. 1971, 8(5), 779-83) in 10.0 ml of N,N-dimethyl-formamide. The reaction mixture was stirred at room temperature for 64 hours and at 80° C. for 5 hours. It was subsequently poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 9:1 to 0:10 v/v gradient of hexane and ethylacetate as the eluent giving 0.308 g (1.0 mmol, 100% of theory) of the 5-(2-hydroxy-ethylamino)-3-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-pyrazine-2-carbonitrile as light yellow amorphous solid; MS: 310 (M+H)+.

Workup

extractionextracted 3 times with 50 ml of dichloromethane
dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
customevaporated under reduced pressure
customThe residue formed
customwas chromatographed on silica gel with a 9:1 to 0:10 v/v gradient of hexane and ethylacetate as the eluent

Sources & evidence

ORD record: ord-365ede64f4e147688d4caef3b54cecb4
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586422B2

Reaction notes

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