1-Methylpiperazine → N-(2,4-difluorophenyl)-N-methyl-8-(4-methylpiperazin-1-yl)-4H-thieno[3,2-c]chromene-2-carboxamide

HRID 628110Notes

Reaction equation

HRID 628110 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]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[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]([N:31]4[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]4)[CH:11]=[CH:10][C:9]=3[O:8][CH2:7][C:6]=2[CH:12]=1)=[O:16]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 579003378-bromo-N-(2,4-difluorophenyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

Product 1

HCID 44242026N-(2,4-difluorophenyl)-N-methyl-8-(4-methylpiperazin-1-yl)-4H-thieno[3,2-c]chromene-2-carboxamide

Procedure

Following Example 70 and General Procedure D, 8-bromo-N-(2,4-difluorophenyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide 160bp and N-methylpiperazine were reacted to give 128bp. 1H NMR (400 MHz, CDCl3) δ 7.30 (m, 1H), 6.94-7.00 (m, 2H), 6.85 (m, 1H), 6.75-6.82 (m, 2H), 6.68 (s, 1H), 5.03 (s, 2H), 3.69 (m, 2H), 3.46 (m, 2H), 3.39 (s, 3H), 3.30 (m, 2H), 3.07 (m, 2H), 2.90 (s, 3H). LCMS (ESI) m/z: 456.2.

Workup

  1. customwere reacted
  2. customto give 128bp

Sources & evidence

ORD record
ord-dc178fbec8de4587afb87ef858fc36df
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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