4-Toluenesulfonyl chloride → HCID 10099270, compound

HRID 858062Notes

Reaction equation

HRID 858062 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]=4F)[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.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>>[CH2:17]([N:12]1[C:13](=[O:16])[C:14]2[NH:15][C:7]([CH2:6][C:5]3[CH:30]=[CH:31][C:2]([NH:1][S:38]([C:35]4[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=4)(=[O:40])=[O:39])=[CH:3][CH:4]=3)=[N:8][C:9]=2[N:10]([CH2:26][CH2:27][CH2:29][CH3:28])[C:11]1=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 218917373-Cyclopropylmethyl-8-[4-aminobenzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione

Product 1

HCID 10099270HCID 10099270, compound

Procedure

8-(4-Amino-benzyl)-3-cyclopropylmethyl-1-(2-fluoro-benzyl)-3,7-dihydro-purine-2,6-dione was condensed with 4-toluenesulfonyl chloride under the conditions previously described to give the stated sulfonamide as an off white solid (59%); 1H NMR(DMSO-d6, 300 MHz) δ13.49 (s, 1H), 10.28 (s, 1H), 7.70 (d, J=8.1 Hz, 2H), 7.45–7.25 (m, 7H), 7.21 (d, J=8.4 Hz, 2H), 7.09 (d, J=8.4 Hz, 2H), 5.12 (s, 2H), 4.02 (s, 2H), 4.01 (t, J=7.0 Hz, 2H), 2.39 (s, 3H), 1.75–1.60 (m, 2H), 1.40–1.25 (m, 2H), 0.94 (t, J=7.5 Hz, 3H); EI-HRMS m/e calculated for C30H31N5O4S (M+) 557.2097, found 557.2090.

Sources & evidence

ORD record
ord-03b2b29e11024331a5b697e0edea7d05
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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