HCID 178501825, compound → HCID 178525996, compound

HRID 1297147Notes

Reaction equation

C(N1C=C(C(=O)C=C(O)C(OC)=O)C(=O)N(CC2C=CC=CC=2)C1=O)C1C=CC=CC=1.[F:32][C:33]1[CH:64]=[CH:63][C:36]([CH2:37][N:38]2[CH:43]=[C:42]([C:44](=[O:52])[CH:45]=[C:46]([OH:51])[C:47]([O:49]C)=[O:48])[C:41](=[O:53])[N:40]([CH2:54][C:55]3[CH:60]=[CH:59][C:58]([F:61])=[CH:57][CH:56]=3)[C:39]2=[O:62])=[CH:35][CH:34]=1>>[F:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:37][N:38]2[CH:43]=[C:42]([C:44](=[O:52])[CH:45]=[C:46]([OH:51])[C:47]([OH:49])=[O:48])[C:41](=[O:53])[N:40]([CH2:54][C:55]3[CH:56]=[CH:57][C:58]([F:61])=[CH:59][CH:60]=3)[C:39]2=[O:62])=[CH:63][CH:64]=1

Participants

Reactant 2

HCID 178501825HCID 178501825, compound

HCID 178501830HCID 178501830, compound

Product 1

HCID 178525996HCID 178525996, compoundYield 49.7%

Procedure

The title compound was synthesized using a similar procedure to that described in Example 2, except that methyl 4-(1,3-dibenzyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-5-yl)-2-hydroxy-4-oxobut-2-enoate was replaced with methyl 4-[1,3-bis(4-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-5-yl]-2-hydroxy-4-oxobut-2-enoate (3c). The title compound was crystalized from hexane and ethyl acetate (3:1). The yield was 49.7%. Mp. 186-188° C. 1HNMR (DMSO-d6): 15.07 (br, s, 1H), 14.02 (br, s, 1H), 8.90 (s, 1H), 7.56 (s, 1H), 7.34-7.46 (m, 4H), 7.10-7.21 (m, 4H), 5.13 (s, 2H), 4.98 (s, 2H). 13CNMR (DMSO-d6): 185.8, 169.2, 163.1, 161.8 (d, J=244.1 Hz), 161.3 (d, J=243.2 Hz), 159.7, 150.8, 150.1, 132.6 (d, J=2.9 Hz), 131.8 (d, J=3.4 Hz), 130.2 (d, J=8.2 Hz), 129.9 (d, J=8.2 Hz), 115.4 (d, J=21.6 Hz), 115.0 (d, J=21.0 Hz), 107.7, 100.7, 52.1, 43.5. FAB-HRMS: [M+H]+ calcd. for C22H17F2N2O6 443.1055, found 443.1044.

Workup

customThe title compound was crystalized from hexane and ethyl acetate (3:1)

Sources & evidence

ORD record: ord-22a4826037ce44a3ad2d4ff91ae6ae88
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250421B2

Reaction notes

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