9-Borabicyclo(3.3.1)nonane → HCID 57537675, compound

HRID 1693735Notes

Reaction equation

HRID 1693735 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([C:14](=[O:20])[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])[CH:11]=[N:12][CH:13]=2)=[CH:6][N:5]=[C:4]2[NH:21][CH:22]=[C:23]([C:24]3[C:25]([NH:30][CH3:31])=[N:26][CH:27]=[CH:28][CH:29]=3)[C:3]=12.B1C2CCCC1CCC2>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:14]([OH:20])[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])[CH:11]=[N:12][CH:13]=2)=[CH:6][N:5]=[C:4]2[NH:21][CH:22]=[C:23]([C:24]3[C:25]([NH:30][CH3:31])=[N:26][CH:27]=[CH:28][CH:29]=3)[C:3]=12

Participants

4

Reactant 2

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 57537508HCID 57537508, compound

Product 1

HCID 57537675HCID 57537675, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-{5-[4-chloro-3-(2-methylamino-pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-N,N-dimethyl-2-oxo-acetamide (35 mg, 0.08 mmol), 9-BBN-dimer (98 mg, 0.4 mmol) in toluene (5 ml) was stirred at 60° C. overnight. The solvent was removed under vacuum and the crude was dissolved in DMSO, filtered and purified by reverse phase HPLC, lyophilized afforded 2-{5-[4-chloro-3-(2-methylamino-pyridin-3-yl)-1H-pyrrolo[2,3-b]-pyridin-5-yl}-pyridin-3-yl]-2-hydroxy-N,N-dimethyl-acetamide (18 mg, 50% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.74 (d, 3H), 2.85 (s, 3H), 2.96 (s, 3H), 5.68 (m, 1H), 5.82 (s, 1H), 6.53 (d, 1H), 7.28 (d, 1H), 7.62 (s, 1H), 7.84 (m, 1H), 8.02 (d, 1H), 8.24 (s, 1H), 8.58 (m, 2H), 12.26 (s, 1H). MS: m/z 437.3 (M+H+).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe crude was dissolved in DMSO
  3. filtrationfiltered
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-af64f5094eb74d1b836d070a28fb4940
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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