8-Quinolinesulfonyl chloride → HCID 11758437, compound

HRID 858060Notes

Reaction equation

HRID 858060 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.[N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][C:40]=2[S:42](Cl)(=[O:44])=[O:43])[CH:35]=[CH:34][CH:33]=1>>[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:42]([C:40]5[CH:39]=[CH:38][CH:37]=[C:36]6[C:41]=5[N:32]=[CH:33][CH:34]=[CH:35]6)(=[O:43])=[O:44])=[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

3

Reactant 2

HCID 292208-Quinolinesulfonyl chlorideHCID 218917373-Cyclopropylmethyl-8-[4-aminobenzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione

Product 1

HCID 11758437HCID 11758437, compound

Procedure

This compound was prepared by the routes shown in schemes 2 and 4. 8-(4-Amino-benzyl)-3-cyclopropylmethyl-1-(2-fluoro-benzyl)-3,7-dihydro-purine-2,6-dione was condensed with 8-quinolinesulfonyl chloride under standard conditions to give the stated sulfonamide. Recrystallization from acetonitrile gave the pure product as an off white solid (53%); 1H NMR(DMSO-d6, 300 MHz) δH13.45 (s, 1H), 10.12 (s, 1H), 9.21 (dd, J=4.2, 1.1 Hz, 1H), 8.59 (dd, J=8.4, 1.8 Hz, 1H), 8.41 (dd, J=7.3, 1.5 Hz, 1H), 8.33 (dd, J=7.7, 1.5 Hz, 1H), 7.82–7.73 (m, 2H), 7.45–7.00 (m, 8H), 5.16 (s, 2H), 3.93 (s, 2H), 3.86 (d, J=7.3 Hz, 2H), 1.30–1.10 (m, 1H) and 0.50–0.30 (m, 4H); EI-HRMS m/e calculated for C32H27FN6O4S (M+) 610.1798, found 610.1804.

Workup

  1. customThis compound was prepared by the routes

Sources & evidence

ORD record
ord-8a8535b92693446a93a3c83dda52f05d
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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