1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 70351445, compound

HRID 231979Notes

Reaction equation

[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([NH2:16])(=[O:15])=[O:14])[CH:5]=[N:4][CH:3]=[N:2]1.C1([O:23][C:24](=O)[NH:25][C:26]2[N:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[N:27]=2)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>O1CCOCC1.O>[CH3:33][O:32][C:30]1[CH:29]=[C:28]([O:34][CH3:35])[N:27]=[C:26]([NH:25][C:24]([NH:16][S:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:1]2[CH2:5][N:4]=[CH:3][NH:2]2)(=[O:15])=[O:14])=[O:23])[N:31]=1

Participants

Conditions

Temperature: 25 °C

Procedure

By the procedure of Example 4, 0.4 g of the product of Example 7 was reacted with 0.52 g of phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate and 0.26 g of "DBU" in 10 ml of p-dioxane. After stirring at 25° C. for two hours, the resulting suspension was diluted with about 50 ml of water, and filtered; the resulting filtrate was acidified with concentrated hydrochloric acid to pH 4, then filtered. The residue was washed 2×10 ml water, suction-dried 16 hours, then triturated with about 10 ml of warm ethyl acetate to yield 0.5 g of the subject compound; m.p. 219°-220° C. IR(nujol): 1690 cm-1 (c=o); NMR(CDCl3): ppm 3.9(S, 6H, OCH3); 5.8(S, 1H, py H); 6.0(S, 2H, CH2); 7.9 and 8.2(2S, 2H, tri 2H); 7.1-7.6(m, 4H, Ar+NH); 8.15(m, 1H, Ar).

Workup

filtrationfiltered
filtrationfiltered
washThe residue was washed 2×10 ml water
customsuction-dried 16 hours
customtriturated with about 10 ml of warm ethyl acetate

Sources & evidence

ORD record: ord-c2c3c017f0264fada18f5b647e3c46b0
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851030

Reaction notes

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