Water → HCID 23447319, compound

HRID 1840542Notes

Reaction equation

HRID 1840542 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:18](=[O:29])[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.S(O)(O)(=O)=O.CS[C:37](=[NH:39])[NH2:38].CSC(=N)N.C(N(CC)CC)C.O>CN(C=O)C>[ClH:2].[C:37]([N:26]1[CH2:27][CH2:28][CH:23]([CH2:22][N:19]2[CH2:20][CH2:21][N:16]([S:13]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([Cl:2])[CH:4]=4)[CH:9]=3)(=[O:15])=[O:14])[CH2:17][C:18]2=[O:29])[CH2:24][CH2:25]1)(=[NH:38])[NH2:39]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 13347Bis(S-methylisothiouronium) sulfate2×HCID 23447373HCID 23447373, compound

Product 1

HCID 23447319HCID 23447319, compoundYield 127.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(6-chloronaphthalene-2-sulfonyl)-1-(4-piperidylmethyl)-2-piperazinone hydrochloride (230 mg) in DMF (10 ml) were added S-methylisothiourea hemisulfate (348 mg), triethylamine (0.418 ml) and water (2 ml), and the mixture was stirred at 50° C. overnight. To the mixture was added S-methylisothiourea hemisulfate (348 mg) and triethylamine (0.418 ml), and the mixture was additionally stirred at 50° C. overnight. The solvent was concentrated and purified with CHP20 column chromatography (water:acetonitrile:1 N hydrochloric acid=70:30:1) to give colorless amorphous of the title compound (160 mg).

Workup

  1. stirringthe mixture was additionally stirred at 50° C. overnight
  2. concentrationThe solvent was concentrated
  3. custompurified with CHP20 column chromatography (water:acetonitrile:1 N hydrochloric acid=70:30:1)

Sources & evidence

ORD record
ord-89d0b36bd18e4a4c84751f1b23a49d3d
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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