HCID 178501825, compound → HCID 178525994, compound

HRID 1297148Notes

Reaction equation

HRID 1297148 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]([F:70])([F:69])[C:34]1[CH:68]=[CH:67][C:37]([CH2:38][N:39]2[CH:44]=[C:43]([C:45](=[O:53])[CH:46]=[C:47]([OH:52])[C:48]([O:50]C)=[O:49])[C:42](=[O:54])[N:41]([CH2:55][C:56]3[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][CH:57]=3)[C:40]2=[O:66])=[CH:36][CH:35]=1>>[F:70][C:33]([F:32])([F:69])[C:34]1[CH:68]=[CH:67][C:37]([CH2:38][N:39]2[CH:44]=[C:43]([C:45](=[O:53])[CH:46]=[C:47]([OH:52])[C:48]([OH:50])=[O:49])[C:42](=[O:54])[N:41]([CH2:55][C:56]3[CH:61]=[CH:60][C:59]([C:62]([F:63])([F:64])[F:65])=[CH:58][CH:57]=3)[C:40]2=[O:66])=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 178501825HCID 178501825, compoundHCID 178501829HCID 178501829, compound

Product 1

HCID 178525994HCID 178525994, compoundYield 68.2%

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-(trifluoromethyl)benzyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-5-yl]-2-hydroxy-4-oxobut-2-enoate (3d). The title compound was recrystalized from hexane and ethyl acetate (3:1). The yield was 68.2%. Mp. 176-178° C. 1HNMR (DMSO-d6): 14.98 (br, s, 1H), 14.02 (br, s, 1H), 8.99 (s, 1H), 7.72 (d, 2H, J=8.0 Hz), 7.66 (d, 2H, J=8.5 Hz), 7.59 (d, 2H, J=8.5 Hz), 7.57 (s, 1H), 7.51 (d, 2H, J=8.0 Hz), 5.26 (s, 2H), 5.09 (s, 2H). 13CNMR (DMSO-d6): 185.8, 169.3, 163.1, 159.9, 151.3, 150.2, 141.2, 140.5, 128.4 (q, J=31.5 Hz), 128.3, 128.2, 127.9 (q, J=31.7 Hz), 125.4 (q, J=3.8 Hz), 125.2 (q, J=3.8 Hz), 124.2 (q, J=272.3 Hz), 124.1 (q, J=271.8 Hz), 108.0, 100.7, 52.6, 43.9. FAB-HRMS: [M+H]+ calcd. for C24H17F6N2O6 543.0991, found 543.1003.

Workup

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

Sources & evidence

ORD record
ord-78e809a90b0c4af5b9f006336675a29f
Source dataset
uspto-grants-2007_07
Patent number
US07250421B2

Reaction notes

Loading…