Triethylamine → HCID 59337800, compound

HRID 12463Notes

Reaction equation

HRID 12463 reaction equation
[CH2:1]([N:3]1[C:7]([C:8](O)=[O:9])=[CH:6][N:5]=[C:4]1[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:2].[CH3:21][CH2:22][N:23](CC)[CH2:24][CH3:25].F[P-](F)(F)(F)(F)F.[N:35]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:39]2[CH:40]=[CH:41][CH:42]=CC=2N=N1>C(Cl)Cl>[CH:39]1([N:35]2[CH2:25][CH2:24][N:23]([C:8]([C:7]3[N:3]([CH2:1][CH3:2])[C:4]([C:11]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:14]=[CH:13][CH:12]=4)=[N:5][CH:6]=3)=[O:9])[CH2:22][CH2:21]2)[CH2:40][CH2:41][CH2:42]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 686291571-Ethyl-2-(naphthalen-1-yl)-1H-imidazole-5-carboxylic acid

Product 1

HCID 59337800HCID 59337800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid (105 mg, 0.394 mmol) and 1-cyclobutylpiperazine bistrifluoroacetate (145 mg, 0.394 mmol, 1.0 eq.) are dissolved in DCM (5 ml), and to the solution is added Et3N (4 eq.), followed by BOP coupling regent (183 mg, 0.433 mmol, 1.1 eq.). The resulting mixture is stirred at rt overnight. DCM is evaporated, and the residue is taken up in EtOAc (1.0 ml). The solution is washed thoroughly with water (3.0 ml×3) to remove the by-product from BOP, and then washed with brine. The solution is dried over sodium sulfate, concentrated and purified through PTLC to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.98 (1H, m), 7.92 (1H, dd), 7.44˜7.63 (5H, m), 7.39 (1H, s), 4.05 (2H, q), 3.89 (4H, s, br), 2.80 (1H, m), 2.43 (4H, s, br), 1.50˜2.20 (6H, m), 1.09 (3H, t); LCMS 389 (M+1).

Workup

  1. customDCM is evaporated
  2. washThe solution is washed thoroughly with water (3.0 ml×3)
  3. customto remove the by-product from BOP
  4. washwashed with brine
  5. dry with materialThe solution is dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified through PTLC

Sources & evidence

ORD record
ord-7e7002a68c61423684a943412eae5f7c
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Reaction notes

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