Ammonium Chloride → HCID 86677340, compound

HRID 1842750Notes

Reaction equation

HRID 1842750 reaction equation
[Cl:1][C:2]1[C:3]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][CH:28]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([N:18]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH3:19])=[CH:11][C:10]=2[O:25][CH3:26])=[N:6][CH:7]=1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[NH3:4].[Cl:1][C:2]1[C:3]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][CH:28]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([NH2:15])[C:12]([N:18]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH3:19])=[CH:11][C:10]=2[O:25][CH3:26])=[N:6][CH:7]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 71270140HCID 71270140, compound2×

Product 2

HCID 222AmmoniaYield 2%HCID 86677340HCID 86677340, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]-N′-(2-dimethylaminoethyl)-2-methoxy-N′-methyl-5-nitrobenzene-1,4-diamine (Intermediate 96, 350 mg, 0.71 mmol), iron (236 mg, 4.23 mmol) and NH4Cl (28.3 mg, 0.53 mmol) in ethanol (15 mL) and water (5 mL) were heated at reflux for 1.5 h. The mixture was then cooled and concentrated in vacuo. The residue was triturated in 10% CH3OH in CH2Cl2 (15 mL) for 0.25 h and then filtered. The residues were triturated again with 10% CH3OH in CH2Cl2 (15 mL) and then filtered. The combined filtrates were washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification by FCC, eluting with 5% CH3OH in CH2Cl2 and then 2-5% 7N methanolic ammonia in CH2Cl2 gave the title compound (159 mg, 48%) as a yellow foam; 1H NMR: 2.18 (6H, s), 2.38 (2H, t), 2.66 (3H, s), 2.91 (2H, t), 3.68 (3H, s), 4.54 (2H, s), 6.77 (1H, s), 6.99-7.10 (2H, m), 7.12-7.22 (1H, m), 7.46 (1H, d), 8.25 (1H, s), 8.30-8.40 (2H, m), 8.49 (1H, d), 11.85 (1H, s); m/z: ES+ MH+ 466.6.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in 10% CH3OH in CH2Cl2 (15 mL) for 0.25 h
  6. filtrationfiltered
  7. customThe residues were triturated again with 10% CH3OH in CH2Cl2 (15 mL)
  8. filtrationfiltered
  9. washThe combined filtrates were washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customPurification by FCC
  13. washeluting with 5% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-731a1f52f1eb434a836bff4a9f95ebf5
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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