Dichloromethane → HCID 23641796, compound

HRID 1169595Notes

Reaction equation

HRID 1169595 reaction equation
Cl.[Cl:2][C:3]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:17][C:4]=1[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=1)=[O:8].C(Cl)Cl.CCN(C(C)C)C(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>CN(C1C=CN=CC=1)C.CCOC(C)=O>[Cl:2][C:3]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[CH2:23][CH2:24][N:25]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:26][CH2:27]2)=[CH:17][C:4]=1[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=1)=[O:8]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68767583HCID 68767583, compound

Product 1

HCID 23641796HCID 23641796, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a 20 mL scintillation vial equipped with a stir bar, 1-(2-chloro-5-(piperazin-1-ylmethyl)benzyl)-3-(6-methylpyridin-3-yl)urea hydrochloride salt (367 mg, 654 □mol) and DMAP (2 mg) were sealed with a septum cap and maintained under a positive nitrogen pressure. To the mixture was added 6 mL of anyhydrous CH2Cl2, followed by DIPEA (520 □L, 2.94 mmol) and methanesulfonyl chloride (70 □L, 785 □mol). The reaction mixture was stirred for 16 h. The reaction mixture was diluted with 6 mL of EtOAc. The organic solution was washed with 4 mL each of water and saturated NaCl solution, dried over Na2SO4, filtered and concentrated to afford 1-(2-chloro-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)benzyl)-3-(6-methylpyridin-3-yl)urea as beige foam (209 mg).

Workup

  1. customIn a 20 mL scintillation vial equipped with a stir bar
  2. customcap
  3. temperaturemaintained under a positive nitrogen pressure
  4. washThe organic solution was washed with 4 mL each of water and saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5c4d9d6584e84f3dbaa996005a3cf672
Source dataset
uspto-grants-2010_11
Patent number
US07825120B2

Reaction notes

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