Ethyl Acetate → 4'-Trifluoromethylbiphenyl-2-carboxylic acid-[2-(2-cyanoethyl)1,2,3,4-tetrahydroisoquinolin-6-yl]-amide

HRID 1954430Notes

Reaction equation

[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.Br[CH2:31][CH2:32][C:33]#[N:34].C(OCC)(=O)C>CN(C)C1C=CN=CC=1.CN(C=O)C.C(Cl)Cl.CCCCCC>[C:33]([CH2:32][CH2:31][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:6]=2)[CH2:1]1)#[N:34]

Participants

Conditions

Temperature: 70 °C

Procedure

Compound (II) (780 mg, 1.97 mmole), 3-bromopropionitrile (290 mg, 2.17 mmole) and 4-dimethylaminopyridine (264 mg, 2.16 mmole) were combined in 10 mL of DMF and heated to 70° C. for 72 hrs. The reaction was diluted with methylene chloride, washed with water and brine, and then dried over magnesium sulfate. Purification of the residue obtained on evaporation was carried out with silica gel chromatography using a gradient of 10-100% ethyl acetate in hexane as the eluent.

Workup

washwashed with water and brine
dry with materialdried over magnesium sulfate
customPurification of the residue
customobtained on evaporation

Sources & evidence

ORD record: ord-7c770732e71f44c5ae5359c5fda965f9
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121283

Reaction notes

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