N-Acetylsulfanilyl chloride → HCID 10394040, compound

HRID 858061Notes

Reaction equation

HRID 858061 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.[C:32]([NH:35][C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1)(=[O:34])[CH3:33]>>[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:39]5[CH:38]=[CH:37][C:36]([NH:35][C:32](=[O:34])[CH3:33])=[CH:41][CH:40]=5)(=[O:44])=[O:43])=[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 8481N-Acetylsulfanilyl chlorideHCID 218917373-Cyclopropylmethyl-8-[4-aminobenzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione

Product 1

HCID 10394040HCID 10394040, compound

Procedure

8-(4-Amino-benzyl)-3-cyclopropylmethyl-1-(2-fluoro-benzyl)-3,7-dihydro-purine-2,6-dione was condensed with 4-acetamidobenzenesulfonyl chloride under the conditions previously described to give the stated sulfonamide. Recrystallized from acetonitrile to give the pure product as an off-white solid (68%); 1H NMR (DMSO-d6, 300 MHz) δH13.53 (s, 1H), 10.36 (s, 1H), 10.23 (s, 1H), 7.75 (s, 4H), 7.40–7.05 (m, 8H), 5.19 (s, 2H), 4.02 (s, 2H), 3.91 (d, J=7.0 Hz, 2H), 2.13 (s, 3H), 1.35–1.15 (m, 1H) and 0.55–0.35 (m, 4H); EI-HRMS m/e calculated for C31H29FN6O5S (M+) 616.1904, found 616.1922.

Sources & evidence

ORD record
ord-187f68fb4d3341e2b780f5059756a593
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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