(S)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazepan-2-one → (S)-1-((S)-1-(4-(1-cyclopropyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1,3-diazepan-2-one

HRID 219634Notes

Reaction equation

[OH:1][C:2]([CH3:36])([CH3:35])[CH2:3][C@:4]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:10][CH2:9][CH2:8][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])[C:6](=[O:28])[NH:5]1.Br[C:38]1[CH:39]=[CH:40][C:41](=[O:47])[N:42]([CH:44]2[CH2:46][CH2:45]2)[CH:43]=1>>[CH:44]1([N:42]2[C:41](=[O:47])[CH:40]=[CH:39][C:38]([C:16]3[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]4[CH2:8][CH2:9][CH2:10][C@:4]([CH2:3][C:2]([OH:1])([CH3:35])[CH3:36])([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[NH:5][C:6]4=[O:28])[CH3:12])=[CH:18][CH:17]=3)=[CH:43]2)[CH2:46][CH2:45]1

Participants

Reactant 2

HCID 59190387(S)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazepan-2-one

HCID 596357625-Bromo-1-cyclopropylpyridin-2(1H)-one

Product 1

HCID 59190367(S)-1-((S)-1-(4-(1-cyclopropyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1,3-diazepan-2-one

Procedure

The title compound was prepared from (S)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazepan-2-one and 5-bromo-1-cyclopropylpyridin-2(1H)-one following a procedure analogous to that described in Example 11 Step 2. LC-MS Method 1 tR=1.66 min; m/z=500 (M+1). 1H NMR (CD3OD) δ 7.78 (s, 1H), 7.56 (d, 3H), 7.37 (m, 5H), 7.27 (t, 1H), 7.17 (d, 2H), 6.61 (d, 1H), 5.46 (q, 1H), 3.37 (m, 1H), 2.92 (m, 1H), 2.74 (dt, 1H), 2.39 (d, 1H), 1.53 (d, 3H), 1.16 (s, 3H), 0.58 (s, 3H).

Sources & evidence

ORD record: ord-55bb0c3397d54ceabf12ee178dd4f644
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202857B2

Reaction notes

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