1-(Methylsulfonyl)piperazine → HCID 59333532, compound

HRID 421336Notes

Reaction equation

Cl[C:2]1[N:3]([C@H:24]2[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25]2)[C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[N:7]=[C:6]([C:17]1[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=1)[N:5]=2.[S:33]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)([CH3:36])(=[O:35])=[O:34]>CS(C)=O>[CH3:36][S:33]([N:37]1[CH2:42][CH2:41][N:40]([C:2]2[N:3]([C@H:24]3[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:30])=[O:31])[CH2:25]3)[C:4]3[C:9]([N:10]=2)=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:7]=[C:6]([C:17]2[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=2)[N:5]=3)[CH2:39][CH2:38]1)(=[O:35])=[O:34]

Participants

Conditions

Temperature: 140 °C

Procedure

Dimethyl sulfoxide (1 ml) was added to 5-{8-chloro-9-[(3S)-1-(methylsulfonyl)pyrrolidin-3-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (100 mg, 0.21 mmol) and N-mesylpiperazine (171 mg, 1.04 mmol) and the resulting mixture was stirred at 140° C. for 1 hour. The reaction mixture was partitioned with chloroform and water, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=19:1) to give the title compound (105 mg, 83%) as a light brown solid.

Workup

customThe reaction mixture was partitioned with chloroform and water
dry with materialthe organic layer was dried over magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record: ord-67a5d77dbcee446eb43225bbbda8af17
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097622B2

Reaction notes

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