Triethylamine → (4-Isopropyl-piperazin-1-yl)-(4-methyl-5-naphthalen-1-yl-thiazol-2-yl)-methanone

HRID 12454

Reaction equation

HRID 12454 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:17]([OH:19])=O)[S:5][C:6]=1[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH:47]([N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)([CH3:49])[CH3:48].CCN(CC)CC>C(Cl)Cl>[CH:47]([N:50]1[CH2:55][CH2:54][N:53]([C:17]([C:4]2[S:5][C:6]([C:7]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:10]=[CH:9][CH:8]=3)=[C:2]([CH3:1])[N:3]=2)=[O:19])[CH2:52][CH2:51]1)([CH3:49])[CH3:48]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 780131-IsopropylpiperazineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 593378204-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid

Product 1

HCID 59338098(4-Isopropyl-piperazin-1-yl)-(4-methyl-5-naphthalen-1-yl-thiazol-2-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid in methylene chloride (2 ml) is added BOP (44 mg, 0.10 mmol), isopropylpiperazine (13 mg, 0.10 mmol) and Et3N (20 mg, 0.20 mmol). The reaction mixture is stirred at rt for 2 hr. Solvent is removed and the resulting mixture is purified by PTLC to give the title compound. LC-MS M+1 380.03. 1H NMR δ (CDCl3) 7.90-7.96 (m, 2H), 7.68-7.72 (m, 1H), 7.46-7.56 (m, 4H), 4.51 (brs, 2H), 3.85 (brs, 2H), 2.77 (m, 1H), 2.67 (brs, 4H), 2.25 (s, 3H), 1.10 (d, 6H). LC-MS (M+1) 380.1.

Workup

  1. customSolvent is removed
  2. customthe resulting mixture is purified by PTLC

Sources & evidence

ORD record
ord-1fd45a014550457f9029f2a892cfb77e
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Linked notes

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