Hydroxybenzenesulfonic acid → 5-{8-[(3S)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine benzenesulfonate

HRID 421374Notes

Reaction equation

HRID 421374 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]([CH2:32][C:33]([F:36])([F:35])[F:34])[C:12]3[C:17]([N:18]=2)=[C:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:15]=[C:14]([C:25]2[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=2)[N:13]=3)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2].O.[C:39]1([S:45]([OH:48])(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(O)C>[C:39]1([S:45]([OH:48])(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]([CH2:32][C:33]([F:36])([F:35])[F:34])[C:12]3[C:17]([N:18]=2)=[C:16]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[N:15]=[C:14]([C:25]2[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=2)[N:13]=3)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 15619088Hydroxybenzenesulfonic acidHCID 45378171HCID 45378171, compound

Product 1

HCID 866419945-{8-[(3S)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine benzenesulfonateYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-{8-[(3S)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine (53.8 mg, 0.1 mmol) in 10% aqueous ethanol solution (0.6 ml) was added benzenesulfonic acid mono hydrate (20.0 mg, 0.11 mmol) at 50° C., and the mixture was cooled down to room temperature, and was stirred for 5 hr. The solid precipitated out was collected and dried to give 5-{8-[(3S)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine benzenesulfonate (52.4 mg) as a yellow solid.

Workup

  1. customThe solid precipitated out
  2. customwas collected
  3. customdried

Sources & evidence

ORD record
ord-81f3988dae1642a6b5ffbcdff7bc7a34
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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