Ammonium Chloride → N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine

HRID 1842676Notes

Reaction equation

HRID 1842676 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21]([NH:26][C:27]4[CH:32]=[C:31]([N+:33]([O-])=O)[C:30]([C:36]5[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH:41]=5)=[CH:29][C:28]=4[O:43][CH3:44])[N:20]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21]([NH:26][C:27]4[CH:32]=[C:31]([NH2:33])[C:30]([C:36]5[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH:41]=5)=[CH:29][C:28]=4[O:43][CH3:44])[N:20]=3)=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 71239353HCID 71239353, compound2×

Product 1

HCID 86677326N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamineYield 140.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-[1-(benzenesulfonyl)indol-3-yl]-5-chloro-N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]pyrimidin-2-amine (Intermediate 9, 349 mg, 0.47 mmol), iron (157 mg, 2.82 mmol) and NH4Cl (17.60 mg, 0.33 mmol) in ethanol (9 mL) and water (3 mL) was heated at reflux for 1.5 h. The mixture was cooled and concentrated in vacuo. CH2Cl2 (20 mL) and CH3OH (2 mL) were then added and the mixture was stirred for 5 minutes and then filtered. The organic solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (396 mg, 140%) as a green foam which was used without further purification. m/z: ES+ MH+ 601.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additionCH2Cl2 (20 mL) and CH3OH (2 mL) were then added
  6. filtrationfiltered
  7. washThe organic solution was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39656e78de5f4644ac38e7f2baaa35cf
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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