5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride → N-(4-((1-(2-fluorobenzyl)-3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)methyl)phenyl)-5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonamide

HRID 858084Notes

Reaction equation

[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])[C:11](=[O:25])[N:10]([CH2:26][CH2:27][CH2:28][CH3:29])[C:9]=3[N:8]=2)=[CH:4][CH:3]=1.[Cl:32][C:33]1[N:37]([CH3:38])[N:36]=[C:35]([CH3:39])[C:34]=1[S:40](Cl)(=[O:42])=[O:41]>N1C=CC=CC=1>[CH2:26]([N:10]1[C:9]2[N:8]=[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:40]([C:34]4[C:35]([CH3:39])=[N:36][N:37]([CH3:38])[C:33]=4[Cl:32])(=[O:41])=[O:42])=[CH:31][CH:30]=3)[NH:15][C:14]=2[C:13](=[O:16])[N:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:11]1=[O:25])[CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 23 °C

Procedure

8-(4-Amino-benzyl)-3-butyl-1-(2-fluoro-benzyl)-3,7-dihydro-purine-2,6-dione (20 mg, 0.047 mmol) was dissolved in pyridine (0.5 ml) and treated with 5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride (Maybridge, 16 mg, 0.07 mmol). The reaction was stirred at 23° C. for 3 h. The solvent was removed and the residue was purified by reverse phase HPLC. LCMS, m/z (M+H)=615.2.

Workup

customThe solvent was removed
customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-0e6df2be4e8649699c6cae2f33840140
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148229B2

Reaction notes

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