Dimethylamine → N,N-Dimethyl-3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionamide

HRID 8270

Reaction equation

CO[C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:19][N:18]4[CH2:28][CH2:29][CH2:30][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[CH3:32][NH:33][CH3:34].CO.C[Al](C)C.CCCCCC.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>ClCCl>[CH3:32][N:33]([CH3:34])[C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:19][N:18]4[CH2:28][CH2:29][CH2:30][C:17]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionic acid methyl ester (0.30 g, 0.73 mmol) and 2M dimethylamine in methanol (1.05 mL, 2.1 mmol) in dichloromethane (1 mL) is added 2 M trimethylaluminum in hexane (1.64 mL, 3.25 mmol). The solution is heated at 40° C. for 48 h. The mixture is diluted with dichloromethane (150 mL), treated with saturated potassium sodium tartrate (30 mL), and stirred 18 h. The organic portion is separated and; washed with water and brine, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (10% methanol in dichloromethane) to yield the title compound, 0.29 g (89%), as a yellow foam.

Workup

customThe organic portion is separated
washwashed with water and brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue is chromatographed on SiO2 (10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-48783e86a64147d588437490851d74d4
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087626B2

Linked notes

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