methyl (4S)-3-({[3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propyl]amino}carbonyl)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate → Snap-7941

HRID 2213522Notes

Reaction equation

HRID 2213522 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][NH:20][C:21]([N:23]3[C@@H:28]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=4)[C:27]([C:37]([O:39][CH3:40])=[O:38])=[C:26]([CH2:41][O:42][CH3:43])[NH:25][C:24]3=[O:44])=[O:22])[CH2:15][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]>[Pd]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][NH:20][C:21]([N:23]3[C@@H:28]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=4)[C:27]([C:37]([O:39][CH3:40])=[O:38])=[C:26]([CH2:41][O:42][CH3:43])[NH:25][C:24]3=[O:44])=[O:22])[CH2:15][CH2:16]2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 69523367methyl (4S)-3-({[3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propyl]amino}carbonyl)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Product 1

HCID 11520239Snap-7941

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

This radiochemical synthesis was carried out by Amersham Pharmacia Biotech, Cardiff, Wales. A methanolic solution of methyl (4S)-3-({[3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propyl]amino}carbonyl)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate was exposed to tritium gas at 1 atmosphere pressure in the presence of 5% palladium on carbon with stirring overnight to give the tritiated methyl (4S)-3-{[(3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propyl)amino]carbonyl}-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate ((+)-isomer). After purification by reverse phase HPLC (Hypersil ODS, 4.6×100 mm, methanol:H2O:Et3N 10:90:1 to 100:0:1 in 15 min at 1.0 mL/min, with radiochemical and UV detection), this product was used as a radioligand in the MCH1 binding assays. The same procedure was carried out with H2 gas in place of 3H2 to afford the non-radioactive version of Compound A.

Workup

  1. customThis radiochemical synthesis

Sources & evidence

ORD record
ord-4b241be244904c128d3fae565b834584
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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