HCID 22050424, compound → HCID 22050296, compound

HRID 1832109Notes

Reaction equation

HRID 1832109 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:69])[N:37]([C:59]2[CH:60]=[C:61]([CH:65]=[CH:66][C:67]=2[CH3:68])[C:62]([OH:64])=[O:63])[C:38]([CH3:58])=[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]([NH:54][CH:55]1[CH2:57][CH2:56]1)=[O:53]>>[CH:55]1([NH:54][C:52]([NH:51][CH2:50][C:44]2[CH:45]=[C:46]([F:49])[CH:47]=[CH:48][C:43]=2[CH2:42][O:41][C:40]2[CH:39]=[C:38]([CH3:58])[N:37]([C:59]3[CH:60]=[C:61]([CH:65]=[CH:66][C:67]=3[CH3:68])[C:62]([O:64][CH3:2])=[O:63])[C:36](=[O:69])[CH:35]=2)=[O:53])[CH2:57][CH2:56]1

Participants

3

Reactant 2

HCID 22050424HCID 22050424, compoundHCID 220506313-[4-[(4-fluoro-2-{[(methoxycarbonyl)amino]methyl}benzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic Acid

Product 1

HCID 22050296HCID 22050296, 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 8.02 (m, 1H), 7.74 (s, 1H), 7.48 (m, 2H), 7.12 (m, 1H), 7.01 (m, 1H), 6.22 (s, 1H), 6.08 (s, 1H), 5.19 (s, 2H), 4.44 (s, 2H), 2.48 (m, 1H), 2.11 (s, 3H), 1.90 (s, 3H), 0.69 (m, 2H), 0.47 (m, 2H). ES HRMS m/z 480.1921 (M+H calculated for C26H27FN3O5 requires 480.1929). Step 3: Preparation of 3-[3-bromo-4-{[2-({[(cyclopropylamino)carbonyl]amino}methyl)-4-fluorobenzyl]oxy}-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic acid

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f091799274794144974bde3aeba4fc90
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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