Chloroform → HCID 19012158, compound

HRID 1729300Notes

Reaction equation

HRID 1729300 reaction equation
C(Cl)(Cl)[Cl:2].[NH2:5][C:6]1[CH:31]=[CH:30][C:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]([CH3:26])[C:24](=[O:27])[N:23]([CH3:28])[C:22](=[O:29])[CH:21]=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>O>[ClH:2].[CH3:26][N:25]1[C:20]([N:17]2[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][CH2:11][O:10][C:9]3[CH:30]=[CH:31][C:6]([N:5]([S:40]([CH3:39])(=[O:42])=[O:41])[S:40]([CH3:39])(=[O:42])=[O:41])=[CH:7][CH:8]=3)[CH2:19][CH2:18]2)=[CH:21][C:22](=[O:29])[N:23]([CH3:28])[C:24]1=[O:27]

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10090741HCID 10090741, compound

Product 1

HCID 19012158HCID 19012158, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 ml of a chloroform solution containing 1.0 g of 6-[4-(3-[4-aminophenoxy]propyl)piperazin-1-yl]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione obtained in Example 6 and 2.5 ml of triethylamine was added to 5 ml of a chloroform solution containing 1.5 g of methanesulfonyl chloride, and the solution was then stirred at room temperature for 30 minutes. Afterward, water was added to the solution, and this solution was then subjected to separation, drying, concentration and purification through a silica gel column chromatograph (chloroform/methanol=50/1). Next, the thus obtained 1,3-dimethyl-6-[4-(3-[4-dimethanesulfonylaminophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione was treated with an HCl/methanol solution in an ordinary manner to obtain 0.75 g of crystalline 1,3-dimethyl-6-[4-(3-[4-dimethanesulfonylaminophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.hydrochloride (Compound 83).

Workup

  1. customthis solution was then subjected to separation
  2. customdrying
  3. concentrationconcentration and purification through a silica gel column chromatograph (chloroform/methanol=50/1)
  4. additionNext, the thus obtained 1,3-dimethyl-6-[4-(3-[4-dimethanesulfonylaminophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione was treated with an HCl/methanol solution in an ordinary manner

Sources & evidence

ORD record
ord-72540d647e7f4253ac41f87040bd2c4f
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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