Dimethylformamide → HCID 11635391, compound

HRID 916556Notes

Reaction equation

HRID 916556 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH:13]([NH:21][C:22](=[O:24])[CH3:23])[CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.C([N:27]([CH:31]([CH3:33])C)[CH:28]([CH3:30])[CH3:29])C.Cl[N-][C:36]1C=CC=[C:38]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:37]=1.CN(C)C=[O:51]>>[C:22]([NH:21][CH:13]([CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1)[CH2:14][N:15]1[CH2:16][CH2:17][N:18]([CH2:33][C:31]([NH:27][C:28]2[CH:29]=[CH:36][CH:37]=[C:38]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:30]=2)=[O:51])[CH2:19][CH2:20]1)(=[O:24])[CH3:23]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 58960949HCID 58960949, compoundHCID 86603598HCID 86603598, compound

Product 1

HCID 11635391HCID 11635391, compound

Conditions

Temperature
75 °C

Procedure

To a solution of N-[2-(2-methylbenzothiazol-5-yloxy)-1-(piperazinylmethyl)ethyl]-acetamide (18.4 mg) in N,N-dimethylformamide (2 ml) was added ethyldiisopropylamine (500 μl) and chloro-N-(3-phenylphenyl)amide (15.6 mg). The mixture was heated at 75° C. overnight, then solvent removed under reduced pressure, and the residue dissolved in a mixture of methanol/methylene chloride and applied to a preparative TLC plate. The plate was eluted with 4% methanol/methylene chloride and the appropriate fraction collected, providing 2-{4-[2-(acetylamino)-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}-N-(3-phenylphenyl)acetamide (10 mg).

Workup

  1. customsolvent removed under reduced pressure
  2. dissolutionthe residue dissolved in a mixture of methanol/methylene chloride
  3. washThe plate was eluted with 4% methanol/methylene chloride
  4. customthe appropriate fraction collected

Sources & evidence

ORD record
ord-3cae213443e64faab8843f449191a9c0
Source dataset
uspto-grants-2007_09
Patent number
US07271169B2

Reaction notes

Loading…