4-(3-Hexyl-ureido)benzenesulfonyl chloride → N-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenyl]-4-(3-hexyl-ureido)-benzenesulfonamide

HRID 1794846Notes

Reaction equation

HRID 1794846 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:18]([NH:24][C:25](=[O:37])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>>[O:4]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:33]([C:30]4[CH:29]=[CH:28][C:27]([NH:26][C:25]([NH:24][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:37])=[CH:32][CH:31]=4)(=[O:35])=[O:34])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 154719184-(3-Hexyl-ureido)benzenesulfonyl chlorideHCID 222203164-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)aniline

Product 1

HCID 22220284N-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenyl]-4-(3-hexyl-ureido)-benzenesulfonamide

Procedure

The title compound was prepared from 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-phenylamine (which was obtained in Example 214) and 4-(3-hexyl-ureido)benzenesulfonyl chloride (U.S. Pat. No. 5,561,142/1996) according to the procedure of Example 215 as a white flake; 1H NMR (300 MHz, DMSO-d6) δ 0.86 (t, J=6.5 Hz, 3 H), 1.20–1.50 (m, 8 H), 1.65 (t, J=5.7 Hz, 4 H), 3.00–3.10 (m, 2 H), 3.14 (t, J=5.7 Hz, 4 H), 3.88 (s, 4 H), 6.28 (t, J=5.6 Hz, 1 H), 6.79 (d, J=9.0 Hz, 2 H), 6.87 (d, J=9.0 Hz, 2 H), 7.45 (d, J=9.1 Hz, 2 H), 7.51 (d, J=9.1 Hz, 2 H), 8.82 (s, 1 H); MS (ES) m/z: 517.2 (MH+); HRMS Calcd. for C26H37N4O5S (MH+): 517.2485. Found: 517.2377. Anal. Calcd. for C26H36N4O5S: C, 60.44; H, 7.02; N, 10.84. Found: C, 60.29; H, 6.95; N, 10.91.

Sources & evidence

ORD record
ord-8d102f3d83ee4b50a547b5cf74fa1c35
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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