N,N-Dimethylethylenediamine → N-(2,4-difluorophenyl)-8-(2-(dimethylamino)ethylamino)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

HRID 84693Notes

Reaction equation

HRID 84693 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([N:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4[F:26])[CH3:18])=[O:16])[S:14][C:5]=3[C:4]=2[CH:3]=1.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31]>>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[N:17]([CH3:18])[C:15]([C:13]1[S:14][C:5]2[C:4]3[CH:3]=[C:2]([NH:31][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])[CH:11]=[CH:10][C:9]=3[O:8][CH2:7][C:6]=2[CH:12]=1)=[O:16]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 579003378-bromo-N-(2,4-difluorophenyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

Product 1

HCID 44241896N-(2,4-difluorophenyl)-8-(2-(dimethylamino)ethylamino)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

Procedure

Following Example 70 and General Procedure C, 8-bromo-N-(2,4-difluorophenyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide 160bp and N1,N1-dimethyl-1,2-ethanediamine were reacted to give 113bp. 1H NMR (400 MHz, CDCl3), δ: 7.23 (m, 1 H), 6.87-6.92 (m, 2 H), 6.67-6.74 (m, 2 H), 6.47-6.54 (m, 2 H), 4.93 (s, 2 H), 3.84 (m, 2 H), 3.31-3.39 (m, 5 H), 2.86 (s, 6 H). LCMS (ESI) m/z: 444.0

Workup

  1. customwere reacted
  2. customto give 113bp

Sources & evidence

ORD record
ord-c50bc027c03948d7b7721bb4c627eff5
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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