Potassium Carbonate → N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzenesulfonamide

HRID 1278736Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:11]([N:18]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1)[S:19]([C:22]1[CH:27]=[CH:26][C:25](F)=[CH:24][CH:23]=1)(=[O:21])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCN(C)C1=O>[CH2:11]([N:18]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1)[S:19]([C:22]1[CH:27]=[CH:26][C:25]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)=[CH:24][CH:23]=1)(=[O:21])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1,4-Dioxa-8-azaspiro[4.5]decane (0.14 ml, 0.95 mM) was added to a solution of N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-fluoro-benzenesulfonamide(0.19 g, 0.47 mM) and potassium carbonate (0.66 g, 4.82 mM)in anhyrous 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(5 ml). The reaction was stirred at 70° C. for two days. The reaction was quenched with water(50 ml). The precipitate was washed with water and dried under reduced pressure to afford 0.15 g of the desired product as a tan solid. H1 NMR(CDCl3) δ 1.81(t, 4H, J=5.67 Hz), 3.50(t, 4H, J=5.97 Hz), 3.65(s, 3H), 3.81 (s, 3H), 4.01 (s, 4H), 4.66(s, 2H), 6.43(d, 1H, J=2.34 Hz), 6.53(m, 1H), 6.66(d, 1H, J=8.58 Hz), 6.90(d, 1H, J=9.03 Hz), 7.19(m, 6H), 7.53(d, 2H, J=9.00 Hz). MS(ES) m/z 525.0; (MH+); HRMS for C28H32SN2O6: 525.2049.

Workup

customThe reaction was quenched with water(50 ml)
washThe precipitate was washed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-b93097fb29b9418a89bc8672641982dd
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444685B1

Reaction notes

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