Methanesulfonyl chloride → HCID 10097381, compound

HRID 858063Notes

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

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 218917373-Cyclopropylmethyl-8-[4-aminobenzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione

Product 1

HCID 10097381HCID 10097381, compoundYield 28%

Procedure

8-(4-Amino-benzyl)-3-cyclopropylmethyl-1-(2-fluoro-benzyl)-3,7-dihydro-purine-2,6-dione was condensed with methanesulfonyl chloride under the conditions previously described to give the stated sulfonamide as an off-white solid (28%); 1H NMR(DMSO-d6, 300 MHz) δH 13.42 (s, 1H), 9.61 (s, 1H), 7.30–6.90 (m, 8H), 5.04 (s, 2H), 3.94 (s, 2H), 3.77 (d, J=6.6 Hz, 2H), 2.87 (s, 3H), 1.25–1.05 (m, 1H), 0.40–0.25 (m, 4H); EI-HRMS m/e calculated for C24H24FN5O4S (M+) 497.1533, found 497.1528.

Sources & evidence

ORD record: ord-3991b3553e4448fb88576935f9afb15c
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148229B2

Reaction notes

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