Dichloromethane → HCID 89677164, compound

HRID 2278168Notes

Reaction equation

HRID 2278168 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH3:22])[N:17]=[CH:16]4)O)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.C(Cl)Cl.S(Cl)(Cl)=O.[N:30]1([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>C(#N)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH3:22])[N:17]=[CH:16]4)[N:33]3[CH2:32][CH2:31][N:30]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34]3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 89677202HCID 89677202, compound

Product 1

HCID 89677164HCID 89677164, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A round bottom flask was charged with bis(1-methyl-1H-indazol-5-yl)methanol (50 mg, 0.17 mmol) and CH2Cl2 (5 mL). Thionyl chloride (25 μL, 342 mmol) was added, resulting in a cloudy solution. After 15 min the solution become a clear pink solution and was stirred at room temperature for 48 h. The solution was concentrated under reduced pressure. Acetonitrile was added and the solution was concentrated two times. Acetonitrile (7 mL) and tert-butyl piperazine-1-carboxylate (60 mg, 0.32 mmol) was added and the solution was stirred at room temperature overnight. The reaction was concentrated under reduced pressure and purified by silica chromatography (100% CH2Cl2 to 3% MeOH in CH2Cl2) yielding tert-butyl 4-(bis(1-methyl-1H-indazol-5-yl)methyl)piperazine-1-carboxylate (53 mg, 56%) as a light brown oil. 1H NMR 400 MHz (CDCl3) δ 7.97-7.89 (m, 2H), 7.79 (s, 2H), 7.54 (dd, J=8.8, 1.5 Hz, 2H), 7.32 (d, J=8.7 Hz, 2H), 4.49 (s, 1H), 4.03 (s, 6H), 3.47 (s, 4H), 2.41 (s, 4H), 1.45 (s, 9H). LCMS (ESI, m/z): 483 [M+H]+.

Workup

  1. customresulting in a cloudy solution
  2. concentrationThe solution was concentrated under reduced pressure
  3. additionAcetonitrile was added
  4. concentrationthe solution was concentrated two times
  5. stirringthe solution was stirred at room temperature overnight
  6. concentrationThe reaction was concentrated under reduced pressure
  7. custompurified by silica chromatography (100% CH2Cl2 to 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a3904480b8184a3c8e1b0003d9118703
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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