4-Methoxy-o-phenylenediamine → (RS)-1-[2-(5-Methoxy-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone

HRID 598586Notes

Reaction equation

HRID 598586 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][C:23](O)=O)=[O:15])=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([NH2:35])[C:31]([NH2:34])=[CH:32][CH:33]=1>C(OCC)(=O)C>[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]2[NH:34][C:23]([CH2:22][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][N:16]3[C:14]([C:9]3[N:10]=[C:11]([CH3:13])[S:12][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:15])=[N:35][C:30]=2[CH:29]=1

Participants

4

Reactant 2

HCID 1534044-Methoxy-o-phenylenediamineHCID 23146320(1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid

Product 1

HCID 178488065(RS)-1-[2-(5-Methoxy-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoneYield 13%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirring mixture of (1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid, D17 (150 mg, 0.42 mmol) and 4-methoxy-benzene-1,2-diamine (58 mg, 0.42 mmol) was heated at 120° C. for 4 h. The cooled reaction mixture was dissolved in ethyl acetate, washed with sodium hydrogen carbonate (2×) then brine. The solvent was removed in vacuo and the residue was chromatographed (silica gel, ethyl acetate) to afford the title compound as a brown gum (25 mg, 13%).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with sodium hydrogen carbonate (2×)
  3. customThe solvent was removed in vacuo
  4. customthe residue was chromatographed (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-388fcd2c0fc4455fab517ca7452cd4f6
Source dataset
uspto-grants-2011_03
Patent number
US07897618B2

Reaction notes

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