6'-Bromo-5''-methyl-3'H-dispiro[cyclobutane-1,2'-indene-1',2''-imidazol]-4''-amine → US8865911, 57 Isomer 1

HRID 1770977Notes

Reaction equation

HRID 1770977 reaction equation
Br[C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][C:7]3([C:11]42[N:15]=[C:14]([NH2:16])[C:13]([CH3:17])=[N:12]4)[CH2:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1.[C:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[N:27][CH:28]=1)#[C:21][CH3:22]>>[CH3:17][C:13]1[C:14]([NH2:16])=[N:15][C:11]2([C:18]3[C:5](=[CH:4][CH:3]=[C:2]([C:25]4[CH:26]=[N:27][CH:28]=[C:23]([C:20]#[C:21][CH3:22])[CH:24]=4)[CH:19]=3)[CH2:6][C:7]32[CH2:10][CH2:9][CH2:8]3)[N:12]=1

Participants

3

Reactant 2

HCID 573866666'-Bromo-5''-methyl-3'H-dispiro[cyclobutane-1,2'-indene-1',2''-imidazol]-4''-amineHCID 574164825-(1-Propynyl)pyridine-3-boronic Acid (contains varying amounts of Anhydride)2×

Product 1

HCID 57386668US8865911, 57 Isomer 1Yield 68%

Procedure

The title compound (60 mg, 68% yield) was prepared by the method described in Example 55, starting from 6′-bromo-5″-methyl-3′H-dispiro[cyclobutane-1,2′-indene-1′,2″-imidazol]-4″-amine (Example 54) (80 mg, 0.25 mmol) and 5-(prop-1-ynyl)pyridin-3-ylboronic acid (Intermediate 15, 53 mg, 0.33 mmol). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.59 (m, 4H) 1.83 (d, 1H) 2.09 (s, 3H) 2.16 (d, 1H) 2.21 (s, 3H) 3.23 (m, 2H) 6.60 (s, 2H) 6.89 (d, 1H) 7.41 (d, 1H) 7.54 (dd, 1H) 7.91 (t, 1H) 8.52 (d, 1H) 8.67 (d, 1H). MS (ES+) m/z 355 [M+H]+.

Sources & evidence

ORD record
ord-e77d1d6566a644fab0010b25eb945fa8
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

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