3-[4-[(4-fluoro-2-{[(methoxycarbonyl)amino]methyl}benzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic Acid → HCID 21035376, compound

HRID 1832108Notes

Reaction equation

HRID 1832108 reaction equation
F[C:2]1C=CC(COC2C=C(C)N(C3C=C(C=CC=3C)C(O)=O)C(=O)C=2)=C(CNC(OC)=O)C=1.Br[C:35]1[C:36](=[O:68])[N:37]([C:58]2[CH:59]=[C:60]([CH:64]=[CH:65][C:66]=2[CH3:67])[C:61]([OH:63])=[O:62])[C:38]([CH3:57])=[CH:39][C:40]=1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:44]=1[CH2:50][NH:51][C:52]([O:54][CH2:55][CH3:56])=[O:53]>>[CH2:55]([O:54][C:52]([NH:51][CH2:50][C:44]1[CH:45]=[C:46]([F:49])[CH:47]=[CH:48][C:43]=1[CH2:42][O:41][C:40]1[CH:39]=[C:38]([CH3:57])[N:37]([C:58]2[CH:59]=[C:60]([CH:64]=[CH:65][C:66]=2[CH3:67])[C:61]([O:63][CH3:2])=[O:62])[C:36](=[O:68])[CH:35]=1)=[O:53])[CH3:56]

Participants

3

Reactant 2

HCID 220506313-[4-[(4-fluoro-2-{[(methoxycarbonyl)amino]methyl}benzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic AcidHCID 220506653-[3-bromo-4-[(2-{[(ethoxycarbonyl)amino]methyl}-4-fluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic acid

Product 1

HCID 21035376HCID 21035376, compound

Procedure

Prepared using a procedure similar to that used in the preparation of 3-[4-[(4-fluoro-2-{[(methoxycarbonyl)amino]methyl}benzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic acid. 1H NMR (CD3OD/400 MHz) δ 8.03 (m, 1H), 7.74 (s, 1H), 7.48 (m, 2H), 7.11 (m, 1H), 7.03 (m, 1H), 6.21 (s, 1H), 6.08 (s, 1H), 5.18 (s, 2H), 4.38 (s, 2H), 4.08 (q, 2H, J=7.2 Hz), 2.11 (s, 3H), 1.90 (s, 3H), 1.23 (t, 3H, J=7.2 Hz). ES HRMS m/z 469.1738 (M+H calculated for C25H26FN2O6 requires 469.1769). Step 3: Preparation of 3-[3-bromo-4-[(2-{[(ethoxycarbonyl)amino]methyl}-4-fluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic acid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6241ecce49af47d186d666a456032f36
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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