6-((4-Bromophenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide → HCID 66988803, compound

HRID 1944891Notes

Reaction equation

HRID 1944891 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](C2C=CC=C(S(C3C=C4C(=C(C)C=3)N=CC(C(N)=O)=C4NC3C=CC=C(OC)C=3)(=O)=O)C=2)=[CH:5][CH:4]=1.Br[C:42]1[CH:47]=[CH:46][C:45]([S:48]([C:51]2[CH:52]=[C:53]3[C:58](=[C:59]([CH3:61])[CH:60]=2)[N:57]=[CH:56][C:55]([C:62]([NH2:64])=[O:63])=[C:54]3[NH:65][C:66]2[CH:71]=[CH:70][CH:69]=[C:68]([O:72][CH3:73])[CH:67]=2)(=[O:50])=[O:49])=[CH:44][CH:43]=1>>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:42]2[CH:47]=[CH:46][C:45]([S:48]([C:51]3[CH:52]=[C:53]4[C:58](=[C:59]([CH3:61])[CH:60]=3)[N:57]=[CH:56][C:55]([C:62]([NH2:64])=[O:63])=[C:54]4[NH:65][C:66]3[CH:71]=[CH:70][CH:69]=[C:68]([O:72][CH3:73])[CH:67]=3)(=[O:50])=[O:49])=[CH:44][CH:43]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 669882586-((4-Bromophenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamideHCID 66988923HCID 66988923, compound

Product 1

HCID 66988803HCID 66988803, compoundYield 77%

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 64, using Intermediate 63 (1.38 mmol) as substrate. The crude product was triturated in 15 mL of ethyl acetate for 10 min. After cooling to room temperature, the suspension was recovered by filtration and washed with ethyl acetate to give the title compound as a yellowish solid (591 mg, 77% for 3 steps). ES/MS calcd. for C31H28N3O5S+ 554.2. Found m/z=554.3 (M+H)+.

Workup

  1. customThe title compound was synthesized in a manner analogous to
  2. customThe crude product was triturated in 15 mL of ethyl acetate for 10 min
  3. filtrationthe suspension was recovered by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-8defdb65aecd4e0d9ffe7946f7300864
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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