Methanesulfonyl chloride → HCID 10367941, compound

HRID 858064Notes

Reaction equation

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

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 21891802HCID 21891802, compound

Product 1

HCID 10367941HCID 10367941, compoundYield 35%

Procedure

8-(4-Amino-benzyl)-1-benzyl-3-butyl-3,7-dihydro-purine-2,6-dione was condensed with methanesulfonyl chloride under the conditions previously described to give the stated sulfonamide as a pale brown solid (35%); 1H NMR(DMSO-d6, 300 MHz) δH13.54 (s, 1H), 9.76 (s, 1H), 7.45–7.25 (m, 7H), 7.22 (d, J=8.4 Hz, 2H), 5.14 (s, 2H), 4.10 (s, 2H), 4.04 (t, J=7.1 Hz, 2H), 3.03 (s, 3H), 1.80–1.65 (m, 2H), 1.40–1.25 (m, 2H), 0.96 (t, J=7.3 Hz, 3H); EI-HRMS m/e calculated for C24H27N5O4S (M+) 481.1784, found 481.1781.

Sources & evidence

ORD record: ord-b463ccbfaca0447691bb699f3ccff3a1
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148229B2

Reaction notes

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