3-Chloro-5-cyanophenylboronic acid, pinacol ester → 3-(4''-Amino-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-7'-yl)-5-chlorobenzonitrile

HRID 1468241Notes

Reaction equation

HRID 1468241 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)[C:5]#[N:6].Br[C:20]1[CH:37]=[C:36]2[C:23]([CH2:24][CH2:25][C:26]3([C:29]42[N:33]=[C:32]([NH2:34])[C:31]([CH3:35])=[N:30]4)[CH2:28][CH2:27]3)=[CH:22][CH:21]=1>>[NH2:34][C:32]1[C:31]([CH3:35])=[N:30][C:29]2([C:36]3[C:23](=[CH:22][CH:21]=[C:20]([C:8]4[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=4)[C:5]#[N:6])[CH:37]=3)[CH2:24][CH2:25][C:26]32[CH2:27][CH2:28]3)[N:33]=1

Participants

3

Reactant 2

HCID 532171293-Chloro-5-cyanophenylboronic acid, pinacol ester2×HCID 727146587'-Bromo-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

Product 1

HCID 727148433-(4''-Amino-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-7'-yl)-5-chlorobenzonitrileYield 24%

Procedure

The title compound was prepared following the procedure described for Example 2, starting from 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (Intermediate 4, 71 mg, 0.27 mmol) and 7′-bromo-5″-methyl-3′,4′-dihydrodispiro[cyclopropane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 1, 86 mg, 0.27 mmol). The product was purified by preparative HPLC to give the title compound (24 mg, 24% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.08 (td, 1 H), 0.10-0.16 (m, 1 H), 0.24 (ddd, 1 H), 0.49-0.62 (m, 1 H), 1.49 (dt, 1 H), 2.18 (s, 3 H), 2.32-2.44 (m, 1 H), 2.94-3.07 (m, 2 H), 6.53 (br. s, 2 H), 6.73 (d, 1 H), 7.29 (d, 1 H), 7.52 (dd, 1 H), 7.79 (t, 1 H), 7.88 (s, 1 H), 7.98 (t, 1 H); MS (ES+) m/z 375 [M+H]+.

Workup

  1. customThe title compound was prepared
  2. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-fc44c5359c4a44a1811be9bd9f2bddf7
Source dataset
uspto-grants-2015_04
Patent number
US09000184B2

Reaction notes

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