Isopropylamine → HCID 77492458, compound

HRID 444701Notes

Reaction equation

[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[C:7](/[NH:14][CH:15]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)[CH3:16])=[C:8](\[C:12]#[N:13])/[C:9]([OH:11])=O.[CH:22]([NH2:25])([CH3:24])[CH3:23].OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH:14][CH:15]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)[CH3:16])=[C:8]([C:12]#[N:13])[C:9]([NH:25][CH:22]([CH3:24])[CH3:23])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2Z)-3-(3-bromo-2-thienyl)-2-cyano-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylic acid (0.18 g, 0.468 mmol, 1 eq.) in 5 ml of DCM (CH2Cl2) were added isopropylamine (0.083 g, 1.40 mmol, 3 eq.), hydroxybenzotriazole (HOBT) (0.066 g, 0.49 mmol, 1.05 eq.) and diisopropylethylamine (DIPEA) (0.090 g, 0.70 mmol, 1.5 eq.). The reaction was cooled to 0° C. and dicyclohexylcarbodiimide (DCC) (0.101 g, 0.49 mmol, 1.05 eq.) was added. Stirring was allowed overnight and the solid formed removed by filtration. The solvent was removed under reduced pressure and the residual oil submitted to chromatography on silica gel to give 2Z)-3-(3-bromo-2-thienyl)-2-cyano-N-isopropyl-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylamide (0.090 g, 43% yield) as a white solid and a mixture of atropoisomers.

Workup

customthe solid formed
customremoved by filtration
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-6a46019ecc1548ddb00deee41cfeafca
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476197B2

Reaction notes

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