1H-Indazole-5-boronic acid pinacol ester → HCID 68541918, compound

HRID 1441447Notes

Reaction equation

HRID 1441447 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][C@@H:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][N:29]=[CH:28]3)[O:19]1.CC[O:37][C:38]([CH3:40])=[O:39].CO>N.O>[C:38]([OH:37])(=[O:39])/[CH:40]=[CH:14]/[C:9]([OH:19])=[O:8].[NH:30]1[C:31]2[C:27](=[CH:26][C:25]([C:2]3[N:7]=[N:6][C:5]([O:8][C@@H:9]4[CH:14]5[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]5)[CH2:10]4)=[CH:4][CH:3]=3)=[CH:33][CH:32]=2)[CH:28]=[N:29]1

Participants

5

Reactant 3

HCID 177504691H-Indazole-5-boronic acid pinacol esterHCID 21584119Ethylacetate methanolHCID 86598842(3R)-3-[(6-chloropyridazin-3-yl)oxy]quinuclidine

Product 1

HCID 68541918HCID 68541918, compound

Reagents, catalysts & solvents 1

HCID 12896473Azane;hydrateSolvent

Procedure

The product of Example 9A (481 mg, 2.01 mmol) was coupled with the product of Example 49A (968 mg, 3.96 mmol) according to the procedure of Example 26B. The free base of the title product was purified by chromatography (SiO2, EtOAc/MeOH (with 2 v. % NH3.H2O) (385 mg, 1.19 mmol, yield, 59.5%). It was then treated with fumaric acid (134 mg, 1.2 mmol) in 15 ml EtOAc/EtOH (10:1 v.) at room temperature for 16 hours. The title product was obtained as a solid (414.6 mg, yield, 59.7%). 1H NMR (300 MHz, CD3OD) δ 1.90-2.24 (m, 3H) 2.32-2.47 (m, 1H) 2.61-2.70 (m, 1H) 3.32-3.52 (m, 5H) 3.96 (dd, J=13.73, 8.31 Hz, 1H) 5.53-5.60 (m, 1H) 6.69 (s, 2H) 7.36 (d, J=9.49 Hz, 1H) 7.69 (d, J=8.82 Hz, 1H) 8.08 (dd, J=8.82, 1.70 Hz, 1H) 8.16-8.23 (m, 2H) 8.38 (s, 1H) ppm. MS (DCI/NH3) m/z 322 (M+H)+. Anal. Calculated for C18H19N5O.1.4C4O4H4.0.6H2O: C, 57.30; H, 5.26; N, 14.16. Found: C, 57.24; H, 5.08; N, 14.24.

Sources & evidence

ORD record
ord-316fe6e7790d48fa9a4ac1747493d156
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

Loading…