4-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE) → HCID 59674253, compound

HRID 1391541Notes

Reaction equation

HRID 1391541 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:21])[C:9]2[CH:20]=[CH:19][C:12]3[N:13]([CH3:18])[C:14]([S:16][CH3:17])=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:22][S:23]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1)(=[O:25])=[O:24]>C(O)(C)C>[CH3:22][S:23]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:2]2[N:7]=[C:6]([N:8]([CH3:21])[C:9]3[CH:20]=[CH:19][C:12]4[N:13]([CH3:18])[C:14]([S:16][CH3:17])=[N:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:29][CH:28]=1)(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 128439644-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE)HCID 59674197HCID 59674197, compound

Product 1

HCID 59674253HCID 59674253, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (2-Chloro-pyrimidin-4-yl)-methyl-(1-methyl-2-methylsulfanyl-1H-benzoimidazol-5-yl)-amine (3.19 g, 10 mmol), 4-Methanesulfonylmethyl-phenylamine (1.85 g, 10 mmol) and (833 ul, 12N, 10 mmol) was refluxed in isopropanol (100 ml) overnight. The mixture was then concentrated to dryness and the residual was taken into MeOH and stirred with NaHCO3 (3 g) at room temperature for 20 min. and filtered, the filtrate was concentrated and the residual was purified by silica flash gave 3.35 g as a pale yellow solid: LC/MS(m/e) 469.2 [M+H]+, Rt at 1.37 min.

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customthe residual was purified by silica flash
  5. customgave 3.35 g as a pale yellow solid
  6. customat 1.37 min.

Sources & evidence

ORD record
ord-0b5aa6666b104f98bffc82b2376fdca3
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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