Water → HCID 86677233, compound

HRID 1842680Notes

Reaction equation

HRID 1842680 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([NH:17][C:18]3[CH:23]=[C:22]([N+:24]([O-])=O)[C:21]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)=[CH:20][C:19]=3[O:34][CH3:35])[N:11]=2)=[CH:2]1.[NH4+].[Cl-].O.C(Cl)Cl>C(O)C.[Fe].CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([NH:17][C:18]3[CH:23]=[C:22]([NH2:24])[C:21]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)=[CH:20][C:19]=3[O:34][CH3:35])[N:11]=2)=[CH:2]1

Participants

8

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 71269870HCID 71269870, compound2×

Product 1

HCID 86677233HCID 86677233, compoundYield 77.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 4-(1H-indol-3-yl)-N-[2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrophenyl]-5-methylpyrimidin-2-amine (Intermediate 13, 157 mg, 0.33 mmol), iron (111 mg, 1.99 mmol) and NH4Cl (12.41 mg, 0.23 mmol) was heated in ethanol (6 mL) and water (2 mL) at reflux for 2 h. The mixture was then cooled and concentrated in vacuo to give a thick slurry. CH2Cl2 (100 mL) and CH3OH (10 mL) were then added and the mixture was stirred for 0.25 h, then filtered. The filter cake was washed with CH2Cl2 (50 mL) and CH3OH (5 mL) and the combined organic solutions were dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 1-5% methanolic ammonia in CH2Cl2 gave the title compound (113 mg, 77%) as a pale yellow dry film; m/z: ES+ MH+ 444.53.

Workup

  1. temperatureThe mixture was then cooled
  2. concentrationconcentrated in vacuo
  3. customto give a thick slurry
  4. filtrationfiltered
  5. washThe filter cake was washed with CH2Cl2 (50 mL) and CH3OH (5 mL)
  6. dry with materialthe combined organic solutions were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by FCC
  9. washeluting with 1-5% methanolic ammonia in CH2Cl2

Sources & evidence

ORD record
ord-0756ef313b2a4dd497bcc669d7ae1565
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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