Toluene → HCID 11743378, compound

HRID 751303Notes

Reaction equation

C[Al](C)C.C1(C)C=CC=CC=1.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16].C([O:20][C:21]([C:23]1[N:24]=[C:25]2[CH:30]=[CH:29][C:28]([C:31]3[C:35]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[N:37]=4)=[N:34][N:33]4[CH2:43][CH2:44][CH2:45][C:32]=34)=[CH:27][N:26]2[CH:46]=1)=O)C>ClCCl>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH:16][C:21]([C:23]1[N:24]=[C:25]2[CH:30]=[CH:29][C:28]([C:31]3[C:35]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[N:37]=4)=[N:34][N:33]4[CH2:43][CH2:44][CH2:45][C:32]=34)=[CH:27][N:26]2[CH:46]=1)=[O:20]

Participants

Conditions

Temperature: 45 °C

Procedure

Add 2M trimethylaluminum in toluene (0.38 mL, 0.38 mmol) to a solution of N,N-dimethylethylenediamine (0.034 g, 0.38 mmol) in dichloromethane (20 mL). Stir for 20 min and transfer via cannula to a solution of 6-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester (0.1 g, 0.26 mmol) in dichloromethane (20 mL). Heat at 45° C. and stir for 1.5 h. Add saturated aqueous sodium bicarbonate and extract into dichloromethane. Reversed phase chromatography gives the titled compound (0.067 g, 60%) as a white solid. MS ES+ m/e 430.0 (M+1).

Workup

stirringstir for 1.5 h
extractionAdd saturated aqueous sodium bicarbonate and extract into dichloromethane

Sources & evidence

ORD record: ord-ee6b0d395fbc4e3e8bd4c7228caef95f
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405299B2

Reaction notes

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