Isopropyl iodide → HCID 59635761, compound

HRID 1187911Notes

Reaction equation

HRID 1187911 reaction equation
[CH3:1][C:2]([CH3:34])([CH2:5][C@@:6]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[NH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH3:14])[CH2:8][CH2:7]1)[C:3]#[N:4].C([O-])([O-])=O.[Cs+].[Cs+].[CH:41](I)([CH3:43])[CH3:42]>CN(C=O)C>[CH:41]([N:23]1[C:24](=[O:27])[CH:25]=[CH:26][C:21]([C:18]2[CH:19]=[CH:20][C:15]([C@@H:13]([N:9]3[CH2:8][CH2:7][C@:6]([CH2:5][C:2]([CH3:1])([CH3:34])[C:3]#[N:4])([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:11][C:10]3=[O:12])[CH3:14])=[CH:16][CH:17]=2)=[CH:22]1)([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 596356372,2-dimethyl-3-((R)-2-oxo-3-((S)-1-(4-(6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-6-yl)propanenitrile

Product 1

HCID 59635761HCID 59635761, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2-dimethyl-3-((R)-2-oxo-3-((S)-1-(4-(6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-6-yl)propanenitrile (6 mg, 0.013 mmol) was dissolved in DMF (2.5 mL). Cs2CO3 (c.a. 15 mg, excess) and i-PrI (100 μL, excess) were added. The mixture was stirred for 3 h at rt. LC-MS found the reaction was complete. The mixture was purified by prep HPLC to afford 3-((R)-3-((S)-1-(4-(1-isopropyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)-2,2-dimethylpropanenitrile (1.99 mg, 30%). LC-MS Method 1 tR=2.03 min, m/z=498; 1H NMR (CDCl3) 8.35(d, 1H), 7.80(dd, 1H), 7.37(m, 5H), 7.22(d, 2H), 6.92(d, 2H), 6.83(d, 1H), 5.66(q, 1H), 5.22(m, 1H), 2.93(m, 1H), 2.16(s, 2H), 1.55(d, 3H), 1.46(s, 3H), 1.40(d, 6H), 1.33(s, 3H).

Workup

  1. customThe mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-7bb68095513d43989466c694db98a3b8
Source dataset
uspto-grants-2014_03
Patent number
US08673899B2

Reaction notes

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