1,2-Dichloroethane → N-[6-(2-Cyano-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-3-(3,4-dichloro-benzenesulfonylamino)-3-(4-fluoro-phenyl)-propionamide

HRID 32100Notes

Reaction equation

HRID 32100 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([CH:12]=[CH:13][C:14]#[N:15])[CH:5]=[CH:4][C:3]1=2.[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([NH:27][CH:28]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH2:29][C:30](O)=[O:31])(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[Cl:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(Cl)CCl.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:14]([CH:13]=[CH:12][C:6]1[CH:7]=[C:8]2[C:3](=[CH:4][CH:5]=1)[CH:2]([NH:1][C:30](=[O:31])[CH2:29][CH:28]([NH:27][S:24]([C:19]1[CH:20]=[CH:21][C:22]([Cl:23])=[C:17]([Cl:16])[CH:18]=1)(=[O:26])=[O:25])[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[CH2:11][CH2:10][CH2:9]2)#[N:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 454662343-(3,4-Dichlorobenzene-sulfonylamino)-3-(4-fluoro-phenyl)-propionic acidHCID 689266503-(5-Amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-acrylonitrile

Product 1

HCID 68931708N-[6-(2-Cyano-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-3-(3,4-dichloro-benzenesulfonylamino)-3-(4-fluoro-phenyl)-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5-amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-acrylonitrile (100 mg, 0.504 mmol) in CH2Cl2 (10 mL) was added 3-(3,4-dichlorobenzene-sulfonylamino)-3-(4-fluoro-phenyl)-propionic acid (210 mg, 0.554 mmol), HATU (96 mg, 0.252 mmol), EDC (106 mg, 0.55 mmol), and DIEA (0.17 mL, 1.008 mmol). The resulting mixture was stirred at RT for 18 h. Solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel. Elution with Hex:Acetone mixture (75:25) gave final compound. MS m/z: 573.12 (M+H). Calc'd. for C28H24Cl2FN3O3S-572.48.

Workup

  1. customSolvent was evaporated in vacuo
  2. customThe residue was purified by chromatography on silica gel
  3. washElution with Hex

Sources & evidence

ORD record
ord-04f3873dfe6b437eb9510bef7ccacab2
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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