2-Aminothiazole → N-(4-(5-Butyl-2-methoxyphenyl)-1,3-thiazol-2-yl)-4-(2-chloroethyl)benzamide

HRID 1785624Notes

Reaction equation

HRID 1785624 reaction equation
[CH:1]1[N:5]=[C:4]([NH2:6])[S:3][CH:2]=1.[CH3:7][C:8]#N.[Cl:10][CH2:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2N=N1.C[CH2:50][O:51][C:52]([CH3:54])=O>CCN(CC)CC>[CH2:33]([C:32]1[CH:37]=[CH:54][C:52]([O:51][CH3:50])=[C:7]([C:1]2[N:5]=[C:4]([NH:6][C:17](=[O:19])[C:16]3[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][Cl:10])=[CH:21][CH:20]=3)[S:3][CH:2]=2)[CH:8]=1)[CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 5

HCID 21552-AminothiazoleHCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 887124-(2-Chloroethyl)benzoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 86605597N-(4-(5-Butyl-2-methoxyphenyl)-1,3-thiazol-2-yl)-4-(2-chloroethyl)benzamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture containing 3 g of aminothiazole from Preparation 1.2, 10 ml of CH3CN, 2.54 g of 4-(2-chloroethyl)benzoic acid, 1.11 ml of Et3N and 6.1 g of BOP is prepared and stirred for 48 hours. The reaction medium is diluted with EtOAc and then washed with saturated Na2CO3 solution (twice) and with saturated NaCl solution, and then dried over MgSO4 and concentrated to dryness. After trituration from EtOH, the insoluble material formed is removed by filtration and the filtrate is then concentrated to dryness to give 7.7 g of the expected compound. This compound is purified by chromatography on silica, eluting with a toluene/cyclohexane gradient (9/1; v/v) up to pure toluene.

Workup

  1. customis prepared
  2. washwashed with saturated Na2CO3 solution (twice) and with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customAfter trituration from EtOH, the insoluble material formed
  6. customis removed by filtration
  7. concentrationthe filtrate is then concentrated to dryness

Sources & evidence

ORD record
ord-56d02ca67e6945448b432ec28fca6a04
Source dataset
uspto-grants-2009_03
Patent number
US07504511B2

Reaction notes

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