4-Iodo-1-methylpyridin-2(1H)-one → HCID 59635634, compound

HRID 1640802Notes

Reaction equation

HRID 1640802 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:11]2[CH2:16][CH2:15][C@:14]([CH3:23])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:13][C:12]2=[O:24])[CH2:9][CH3:10])=[CH:4][CH:3]=1.I[C:26]1[CH:31]=[CH:30][N:29]([CH3:32])[C:28](=[O:33])[CH:27]=1>>[CH3:23][C@@:14]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:13][C:12](=[O:24])[N:11]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:26]3[CH:31]=[CH:30][N:29]([CH3:32])[C:28](=[O:33])[CH:27]=3)=[CH:3][CH:4]=2)[CH2:9][CH3:10])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 534080094-Iodo-1-methylpyridin-2(1H)-oneHCID 66600475HCID 66600475, compound

Product 1

HCID 59635634HCID 59635634, compound

Procedure

The title compound was prepared from (R)-3-((S)-1-(4-bromophenyl)propyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one following procedures analogous to those described in Example 32 Method 2 Steps 3 and 4 using 4-iodo-1-methylpyridin-2(1H)-one in Step 4. LC-MS Method 1 tR=1.55 min, m/z=417 (M+1); 1H NMR (CDCl3) 7.41 (1H, d, J=7.03 Hz), 7.33 (2H, d, J=8.20 Hz), 7.29-7.19 (5H, m), 7.10 (1H, d, J=8.20), 6.95 (1H, d=1.76), 6.55 (1H, dd, J=2, 7.03 Hz), 5.51 (1H, q, J=6.49, 9.66 Hz), 3.65 (3H, s), 3.00-2.95 (1H, m), 2.44-2.36 (1H, m), 2.33-2.15 (2H, m), 2.06-1.86 (2H, m), 1.64 (3H, s), 1.02 (3H, t, J=7.32 Hz).

Sources & evidence

ORD record
ord-0343911ddda24045baf0ade85e16759d
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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