Methanesulfonic Acid → 2-(4-Carboxypiperidino)-4-(3,4-methylenedioxy-benzyl)amino-6-chloroquinazoline methanesulfonate

HRID 1938552

Reaction equation

HRID 1938552 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:31])[CH:16]=3)[N:11]=2)[CH2:6][CH2:5]1)([OH:3])=[O:2].[CH3:32][S:33]([OH:36])(=[O:35])=[O:34]>O1CCCC1.C(O)C>[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:31])[CH:16]=3)[N:11]=2)[CH2:6][CH2:5]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 53114861-(6-Chloro-4-(3,4-methylenedioxybenzyl)aminoquinazolin-2-yl)piperidine-4-carboxylic acid

Product 1

HCID 211840322-(4-Carboxypiperidino)-4-(3,4-methylenedioxy-benzyl)amino-6-chloroquinazoline methanesulfonateYield 90.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.00 g (4.54 mmol) of the 2-(4-carboxypiperidino)-4-(3,4-methylenedioxybenzylamino)-6-chloroquinazoline prepared in Example 222 was dissolved in a mixture comprising 25 ml of tetrahydrofuran and 25 ml of ethanol under heating, followed by the dropwise addition of 0.31 ml (4.78 mmol) of methanesulfonic acid. The obtained mixture was cooled by allowing to stand to precipitate crystals. The crystals were recovered by filtration, washed with tetrahydrofuran, and air-dried to give 2.21 g of the title compound.

Workup

  1. temperatureunder heating
  2. temperatureThe obtained mixture was cooled
  3. customto precipitate crystals
  4. filtrationThe crystals were recovered by filtration
  5. washwashed with tetrahydrofuran
  6. customair-dried

Sources & evidence

ORD record
ord-b81665562bfd469bb00e23b65d005a11
Source dataset
uspto-grants-1997_12
Patent number
US05693652

Linked notes

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