Isopropyl Acetate → N-cyclopropyl-6-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)nicotinamide

HRID 1046220

Reaction equation

HRID 1046220 reaction equation
[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.Br[C:37]1[CH:48]=[CH:47][C:40]([C:41]([NH:43][CH:44]2[CH2:46][CH2:45]2)=[O:42])=[CH:39][N:38]=1.C(OC(C)C)(=O)C>>[CH:44]1([NH:43][C:41](=[O:42])[C:40]2[CH:47]=[CH:48][C:37]([C:16]3[CH:17]=[CH:18][C:13]([C@@H:11]([N:7]4[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:35])[CH3:34])([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)[O:9][C:8]4=[O:10])[CH3:12])=[CH:14][CH:15]=3)=[N:38][CH:39]=2)[CH2:46][CH2:45]1

Participants

4

Reactant 3

HCID 7915Isopropyl AcetateHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-oneHCID 658091726-bromo-N-cyclopropylpyridine-3-carboxamide

Product 1

HCID 58109739N-cyclopropyl-6-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)nicotinamide

Procedure

The title compound was prepared from (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one and 6-bromo-N-cyclopropylnicotinamide following a procedure analogous to that described in Example 14. LC-MS Method 1 tR=1.74 min, m/z=456.1; 1H NMR (CDCl3) 0.61 (m, 2H), 0.82 (m, 2H), 1.13 (s, 3H), 1.22 (s, 3H), 1.49 (d, 3H), 2.17 (m, 3H), 2.21 (m, 1H), 2.31 (m, 1H), 2.79 (m, 1H), 2.88 (m, 1H), 5.66 (m, 1H), 6.40 (s, 1H), 6.99 (d, 1H), 7.20-7.31 (m, 5H), 7.60 (d, 1H), 7.68 (d, 2H), 8.07 (d, 1H), 8.89 (s, 1H). The compound was dissolved in refluxing isopropyl acetate and allowed to cool slowly to it to afford a solid with mp 191-194° C.

Workup

  1. dissolutionThe compound was dissolved
  2. temperatureto cool slowly to it
  3. customto afford a solid with mp 191-194° C.

Sources & evidence

ORD record
ord-70d692c3e12a4c7baeb463eb131f5be5
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Linked notes

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