Diisopropylethylamine → 6-(N-(3-bromophenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

HRID 1424876Notes

Reaction equation

HRID 1424876 reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:27]=[C:28]([N:32]([C:37]2[C:55]([CH:56]3[CH2:58][CH2:57]3)=[CH:54][C:40]3[C:41]([C:51](O)=[O:52])=[C:42]([C:44]4[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=4)[O:43][C:39]=3[CH:38]=2)[S:33]([CH3:36])(=[O:35])=[O:34])[CH:29]=[CH:30][CH:31]=1.Cl.CN.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Br:25][C:26]1[CH:27]=[C:28]([N:32]([C:37]2[C:55]([CH:56]3[CH2:58][CH2:57]3)=[CH:54][C:40]3[C:41]([C:51]([NH:2][CH3:1])=[O:52])=[C:42]([C:44]4[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=4)[O:43][C:39]=3[CH:38]=2)[S:33]([CH3:36])(=[O:35])=[O:34])[CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1317323236-(N-(3-bromophenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylic acid

Product 1

HCID 1317322626-(N-(3-bromophenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamideYield 79.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (237 mg, 0.624 mmol) was added to a solution of 6-(N-(3-bromophenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylic acid (283 mg, 0.520 mmol), methylamine hydrochloride (70.2 mg, 1.040 mmol) and DIEA (0.318 mL, 1.819 mmol) in DMF (2 mL) at room temperature. The mixture was stirred for one hour. The reaction mixture was diluted with EtOAc. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (hexane:ethyl acetate) to give 6-(N-(3-bromophenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (230 mg, 79%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (s, 1H) 8.12 (s, 1H) 7.96 (dd, J=8.98, 5.47 Hz, 2H) 7.60 (t, J=2.05 Hz, 1H) 7.27-7.54 (m, 5H) 7.18 (s, 1H) 3.41 (s, 3H) 2.82 (d, J=4.69 Hz, 3H) 2.07-2.22 (m, 1H) 0.65-1.09 (m, 3H) 0.41 (m, 1H). LCMS (m/z, ES+)=557, 559 (M+H, M+2).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-a2a193f9d1cf4da49da7b724af54b439
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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