Dichloromethane → HCID 22727243, compound

HRID 2086314Notes

Reaction equation

HRID 2086314 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14]([N:17]1[CH2:22][C:21](=[O:23])[N:20]([NH:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]4[CH:36]=[CH:35][N:34]=[C:33]([CH3:37])[CH:32]=4)[CH2:27][CH2:26]3)[CH:19]([C:38]([OH:40])=[O:39])[CH2:18]1)(=[O:16])=[O:15])[CH:8]=[CH:7]2.[CH2:41](Cl)Cl>>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14]([N:17]1[CH2:22][C:21](=[O:23])[N:20]([NH:24][CH:25]3[CH2:26][CH2:27][N:28]([C:31]4[CH:36]=[CH:35][N:34]=[C:33]([CH3:37])[CH:32]=4)[CH2:29][CH2:30]3)[CH:19]([C:38]([O:40][CH3:41])=[O:39])[CH2:18]1)(=[O:16])=[O:15])[CH:8]=[CH:7]2

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 86759423HCID 86759423, compound

Product 1

HCID 22727243HCID 22727243, compound

Procedure

Methyl 1-[[4-[(6-chloro-2-naphthyl)sulfonyl]-1-[[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate dihydrochloride (1.94 g) obtained in Example 127 was dissolved in methylene chloride (20 ml) and saturated aqueous sodium bicarbonate (20 ml) and partitioned. The organic phase was dried over magnesium sulfate, concentrated under reduced pressure to obtain methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-1-[[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate. This material was dissolved in a 37% aqueous solution of formaldehyde (25.2 ml) and formic acid (12.8 ml), and reflux for 2 hours. The reaction mixture was cooled, made alkaline by adding saturated aqueous sodium bicarbonate, extracted with dichloromethane, dried and then concentrated. The residue was purified on a CHP-20 column (water→1% 1N hydrochloric acid-containing 30% aqueous solution of acetonitrile) and converted into a hydrochloride using a 4 N solution of hydrochloric acid in ethyl acetate (0.15 ml) to obtain the title compound (1.67 g) as a colorless non-crystalline powder.

Workup

  1. customsaturated aqueous sodium bicarbonate (20 ml) and partitioned
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b66004675b1647cf922e8ddae77ad14a
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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