Diisopropylethylamine → 4-{3-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido)-butyric acid ethyl ester

HRID 2247380

Reaction equation

HRID 2247380 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH2:17])=[N:14][C:13]=2[CH3:18])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].CCN(C(C)C)C(C)C.[CH2:28]([O:30][C:31](=[O:38])[CH2:32][CH2:33][CH2:34][N:35]=[C:36]=[O:37])[CH3:29]>C(Cl)Cl>[CH2:28]([O:30][C:31](=[O:38])[CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH:17][C:15]1[S:16][C:12]([C:4]2[CH:5]=[CH:6][C:7]([S:8]([CH3:11])(=[O:9])=[O:10])=[C:2]([F:1])[CH:3]=2)=[C:13]([CH3:18])[N:14]=1)=[O:37])[CH3:29]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3445674Ethyl 4-isocyanatobutyrateHCID 573512775-(3-Fluoro-4-(methylsulfonyl)phenyl)-4-methylthiazol-2-amine

Product 1

HCID 865984314-{3-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-ureido)-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Example 72), (0.1 g, 0.31 mmol) DIPEA (0.039 ml, 0.34 mmol), ethyl-4-isocyanatobutyrate (0.046 ml, 0.31 mmol) in DCM (2 ml) are heated together at reflux overnight. The reaction mixture is diluted with DCM (20 ml) and washed with 1M hydrochloric acid (15 ml), water (2×15 ml), brine (15 ml), dried over MgSO4, filtered and concentrated in vacuo to yield the titled compound as an off white solid.

Workup

  1. temperatureat reflux overnight
  2. washwashed with 1M hydrochloric acid (15 ml), water (2×15 ml), brine (15 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-704a95a01a334b7eb2d6fbfa17200dbb
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Linked notes

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