HCID 178501825, compound → HCID 178525993, compound

HRID 1297146Notes

Reaction equation

HRID 1297146 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][CH:62]=[CH:61][C:34]=1[CH2:35][N:36]1[CH:41]=[C:40]([C:42](=[O:50])[CH:43]=[C:44]([OH:49])[C:45]([O:47]C)=[O:46])[C:39](=[O:51])[N:38]([CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[F:59])[C:37]1=[O:60]>>[F:32][C:33]1[CH:64]=[CH:63][CH:62]=[CH:61][C:34]=1[CH2:35][N:36]1[CH:41]=[C:40]([C:42](=[O:50])[CH:43]=[C:44]([OH:49])[C:45]([OH:47])=[O:46])[C:39](=[O:51])[N:38]([CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[F:59])[C:37]1=[O:60]

Participants

3

Reactant 2

HCID 178501825HCID 178501825, compoundHCID 178501828HCID 178501828, compound

Product 1

HCID 178525993HCID 178525993, compoundYield 56.5%

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(2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-5-yl]-2-hydroxy-4-oxobut-2-enoate (3b). The title compound was crystallized from hexane and ethyl acetate (2:1) to give an off-white solid. The yield was 56.5%. Mp. 178-179° C. 1H NMR(DMSO-d6): 15.00 (br, s, 1H), 14.02 (br, s, 1H), 8.90 (s, 1H), 7.55 (s, 1H), 7.08-7.40 (m, 8H), 5.23 (s, 2H), 5.05 (s, 2H). 13CNMR (DMSO-d6): 185.7, 169.2, 163.0, 160.2 (d, J=246.0 Hz), 159.8 (d, J=244.6 Hz), 159.7, 151.2, 149.9, 130.2, 129.0 (d, J=8.2 Hz), 128.4 (d, J=3.9 Hz), 124.5 (d, J=3.3 Hz), 124.3 (d, J=3.3 Hz), 123.1 (d, J=13.9 Hz), 122.3 (d, J=14.5 Hz), 115.4 (d, J=21.1 Hz), 115.1 (d, J=21.1 Hz), 107.6, 100.7, 47.8 (d, J=3.4 Hz), 38.2 (d, J=4.8 Hz). FAB-HRMS: [M+H]+ calcd. for C22H17F2N2O6 443.1055, found 443.1045.

Workup

  1. customThe title compound was crystallized from hexane and ethyl acetate (2:1)
  2. customto give an off-white solid

Sources & evidence

ORD record
ord-a66a932580ec40d1894b08a5ffcb2725
Source dataset
uspto-grants-2007_07
Patent number
US07250421B2

Reaction notes

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