2-(Methylamino)ethanol → HCID 24985303, compound

HRID 1675698Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:39]=[CH:38][C:13]([C:14]([NH:16][CH2:17][C:18]2[C:19]([NH:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[C:20]3[CH:28]=[N:27][N:26]([CH2:29][CH3:30])[C:21]3=[N:22][C:23]=2[CH2:24][CH3:25])=[O:15])=[CH:12][CH:11]=1.[CH3:40][NH:41][CH2:42][CH2:43][OH:44].C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:29]([N:26]1[C:21]2=[N:22][C:23]([CH2:24][CH3:25])=[C:18]([CH2:17][NH:16][C:14](=[O:15])[C:13]3[CH:38]=[CH:39][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:41]([CH2:42][CH2:43][OH:44])[CH3:40])=[CH:11][CH:12]=3)[C:19]([NH:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[C:20]2[CH:28]=[N:27]1)[CH3:30]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 4-(8-bromooctyl)-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide (36.3 mg, 0.06 mmol, e.g. which can be as prepared in Intermediate 41) in N,N-dimethylformamide (6 ml) was treated with 2-(methylamino)ethanol (0.0195 ml, 0.24 mmol, commercially available e.g. from Aldrich) and N,N-diisopropylethylamine (0.042 ml, 0.24 mmol) and heated at 60° C. for 16 hours. The solvent was evaporated and the residue purified by mass directed preparative HPLC (Method A). Fractions containing product were pooled and evaporated to give the title compound (7 mg). LCMS showed MH+=593; TRET=2.37 min.

Workup

customThe solvent was evaporated
customthe residue purified by mass
additionFractions containing product
customevaporated

Sources & evidence

ORD record: ord-c5ec5516f64242f790e82ead7d007021
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003663B2

Reaction notes

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