Toluene → HCID 11717570, compound

HRID 12447Notes

Reaction equation

HRID 12447 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[S:16][C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH3:27])=O)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C1(C)C=CC=CC=1>C1COCC1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([CH2:10][C:12]2[S:16][C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH3:27])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1140TolueneHCID 11995934HCID 11995934, compound

Product 1

HCID 11717570HCID 11717570, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-isopropyl-piperazin-1-yl)-(4-methyl-2-naphthalen-1-yl-thiazol-5-yl)-methanone (25 mg, 0.066 mmol) in anhydrous THF (2.5 ml) is added a solution of alane-dimethylethylamine complex in toluene (0.5 M, 0.4 ml, 0.2 mmol, 3.0 eq.) dropwise at 0° C. The resulting mixture is stirred at rt overnight. The reaction is quenched with one drop of water, followed by one drop of 10 N sodium hydroxide solution and two more drops of water. The resulting mixture is diluted with EtOAc (10 ml), dried over magnesium sulfate, and concentrated. The residue is purified through PTLC (EtOAc/Et3N, 25:1) to give the desired product. 1H NMR (300 MHz, CDCl3) δ 8.78 (1H, dd), 7.89 (2H, m), 7.78 (1H, dd), 7.60˜7.45 (3H, m), 3.74 (2H, s), 2.76˜2.54 (9H, m, overlapped), 2.51 (3H, s), 1.06 (6H, d); LC-MS (M+1) 366.2.

Workup

  1. customThe reaction is quenched with one drop of water
  2. additionThe resulting mixture is diluted with EtOAc (10 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified through PTLC (EtOAc/Et3N, 25:1)

Sources & evidence

ORD record
ord-cf0db1431780443d91e0f14adfb30a9a
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Reaction notes

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