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

HRID 504062Notes

Reaction equation

HRID 504062 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-chloro-ethyl)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-57e6b924b2c74a9b854c9d3d0c97fdae
Source dataset
uspto-grants-2010_08
Patent number
US07777041B2

Reaction notes

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