p-Toluenesulfonic acid monohydrate → HCID 71269870, compound

HRID 1842681Notes

Reaction equation

HRID 1842681 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[C:7]([N+:17]([O-:19])=[O:18])=[CH:6][C:4]=1[NH2:5].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl[C:33]1[N:38]=[C:37]([C:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][CH:40]=2)[C:36]([CH3:48])=[CH:35][N:34]=1>CC(O)CCC>[NH:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:39]([C:37]2[C:36]([CH3:48])=[CH:35][N:34]=[C:33]([NH:5][C:4]3[CH:6]=[C:7]([N+:17]([O-:19])=[O:18])[C:8]([N:10]4[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]4)=[CH:9][C:3]=3[O:2][CH3:1])[N:38]=2)=[CH:40]1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 580714243-(2-Chloro-5-methylpyrimidin-4-yl)-1H-indole2×HCID 86677327HCID 86677327, compound2×

Product 1

HCID 71269870HCID 71269870, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A mixture of 2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitroaniline (Intermediate 14, 204 mg, 0.77 mmol), p-toluene sulphonic acid monohydrate (291 mg, 1.53 mmol) and 3-(2-chloro-5-methylpyrimidin-4-yl)-1H-indole (Intermediate 17, 192 mg, 0.77 mmol) were heated at 120° C. in 2-pentanol (15 mL) for 24 h, resulting in a dark brown suspension. The mixture was then concentrated in vacuo and the resulting residue was dissolved in a mixture of CH2Cl2 and CH3OH (50 mL and 5 mL) and this solution was concentrated onto silica in vacuo. Purification by FCC, eluting with 1-5% methanolic ammonia in CH2Cl2 gave the title compound (157 mg, 43%) as an orange gum; m/z: ES+ MH+ 474.24.

Workup

  1. customresulting in a dark brown suspension
  2. concentrationThe mixture was then concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in a mixture of CH2Cl2 and CH3OH (50 mL and 5 mL)
  4. concentrationthis solution was concentrated onto silica in vacuo
  5. customPurification by FCC
  6. washeluting with 1-5% methanolic ammonia in CH2Cl2

Sources & evidence

ORD record
ord-8515e1ee70e44717822799697ce7f5dd
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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