2-amino-N-methylacetamide hydrochloride → (+)n-[(1S)-1-(aminocarbonyl)ethyl]-3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6h)-yl]-4-methylbenzamide

HRID 1713209Notes

Reaction equation

[Br:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:12]([NH:14][CH2:15][C:16]([NH:18]C)=[O:17])=[O:13])[C:5]([CH3:24])=[N:4][C:3]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34].Cl.[CH3:36]NC(=O)CN>>[NH2:18][C:16]([C@@H:15]([NH:14][C:12](=[O:13])[C:11]1[CH:20]=[CH:21][C:22]([CH3:23])=[C:9]([N:6]2[C:7](=[O:8])[C:2]([Br:1])=[C:3]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[F:34])[N:4]=[C:5]2[CH3:24])[CH:10]=1)[CH3:36])=[O:17]

Participants

Reactant 2

HCID 138422022-amino-N-methylacetamide hydrochloride

HCID 21088988(+/-) 3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6H)-yl]-4-methyl-N-{1-[(methylamino)carbonyl]methyl}benzamide

Product 1

HCID 21089027(+)n-[(1S)-1-(aminocarbonyl)ethyl]-3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6h)-yl]-4-methylbenzamideYield 45%

Procedure

The title compound was prepared by employing a similar procedure as described for (±) 3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6H)-yl]-4-methyl-N-{1-[(methylamino)carbonyl]methyl}benzamide, substituting S-alanineamide hydrochloride for N-methylglycineamide hydrochloride. Yield 45%: 1H NMR (CD3OD/400 MHz) δ 7.96 (m,1H), 7.73 (dd, 1H, J=2.0 Hz), 7.62 (m, 1H), 7.55 (d, 1H, J=8.0 Hz), 7.01 (m, 2H), 5.56 (abq, 2H), 4.55 (abq, 1H), 2.18 (s, 3H), 2.14 (s, 3H), and 1.45 (d, 3H, J=7.2 Hz); ES-HRMS m/z 535.0757 (M+H calcd for C23H22N4O4F2 Br requires 535.0787). 19F NMR (CD3OD/400 MHz) −111.86 (m) and −115.90 (m).

Sources & evidence

ORD record: ord-c6d79fe76808480abcd090f80d035028
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795271B2

Reaction notes

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