2,2-dimethyl-3-((R)-2-oxo-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-6-yl)propanenitrile → 2-(4-((S)-1-((R)-6-(2-cyano-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-N-cyclopropylthiazole-5-carboxamide

HRID 1046085Notes

Reaction equation

[CH3:1][C:2]([CH3:36])([CH2:5][C@@:6]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][CH:16]=2)[CH3:14])[CH2:8][CH2:7]1)[C:3]#[N:4].Br[C:38]1[S:39][C:40]([C:43]([NH:45][CH:46]2[CH2:48][CH2:47]2)=[O:44])=[CH:41][N:42]=1>>[C:3]([C:2]([CH3:36])([CH3:1])[CH2:5][C@@:6]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]2[CH:16]=[CH:17][C:18]([C:38]3[S:39][C:40]([C:43]([NH:45][CH:46]4[CH2:47][CH2:48]4)=[O:44])=[CH:41][N:42]=3)=[CH:19][CH:20]=2)[CH3:14])[CH2:8][CH2:7]1)#[N:4]

Participants

Reactant 2

HCID 596356852,2-dimethyl-3-((R)-2-oxo-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-6-yl)propanenitrile

HCID 67019715HCID 67019715, compound

Product 1

HCID 442514182-(4-((S)-1-((R)-6-(2-cyano-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-N-cyclopropylthiazole-5-carboxamide

Procedure

The title compound was prepared from 2,2-dimethyl-3-((R)-2-oxo-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-6-yl)propanenitrile and 2-bromo-N-cyclopropylthiazole-5-carboxamide following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.262 min, m/z=529.3; 1H NMR (CDCl3) 0.63 (m, 2H), 0.86 (m, 2H), 1.30 (s, 3H), 1.43 (s, 3H), 1.52 (d, 3H), 2.02 (s, 2H), 2.29 (m, 1H), 2.81-2.99 (m, 2H), 5.62 (m, 1H), 6.50 (s, 1H), 6.89 (d, 2H), 7.37 (m, 5H), 7.60 (m, 2H), 8.14 (s, 1H)

Sources & evidence

ORD record: ord-9aff989d188742829173c8d25fcd335c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569292B2

Reaction notes

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