1-(Methylsulfonyl)piperazine → HCID 59333630, compound

HRID 1876504Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:28][CH:29]2[CH2:31][CH2:30]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[C:18]([C:24]([F:27])([F:26])[F:25])=[N:19][C:20]([NH2:23])=[N:21][CH:22]=1)[N:5]=2.[CH3:32][S:33]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)(=[O:35])=[O:34]>CN1CCCC1=O>[CH:29]1([CH2:28][N:3]2[C:2]([N:39]3[CH2:40][CH2:41][N:36]([S:33]([CH3:32])(=[O:35])=[O:34])[CH2:37][CH2:38]3)=[N:10][C:9]3[C:4]2=[N:5][C:6]([C:17]2[C:18]([C:24]([F:26])([F:27])[F:25])=[N:19][C:20]([NH2:23])=[N:21][CH:22]=2)=[N:7][C:8]=3[N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH2:31][CH2:30]1

Participants

Conditions

Temperature: 150 °C

Procedure

N-Methylpyrrolidone (1 ml) was added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-(trifluoromethyl)pyrimidin-2-amine (75 mg, 0.16 mmol) and N-methanesulfonylpiperazine (135 mg, 0.8 mmol) and the resulting mixture was stirred at 150° C. for 7 hours. The reaction mixture was partitioned with ethyl acetate and water and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by preparative HPLC (column; NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (45 mg, 47%) as a white solid.

Workup

customThe reaction mixture was partitioned with ethyl acetate and water
washthe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by preparative HPLC (column; NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid)

Sources & evidence

ORD record: ord-82dfdb877e5044bfb6c645967e9ee358
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309546B2

Reaction notes

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