2-(Methylamino)ethanol → HCID 24985474, compound

HRID 1675700Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][C:12]1[CH:41]=[CH:40][CH:39]=[CH:38][C:13]=1[C:14]([NH:16][CH2:17][C:18]1[C:19]([NH:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[C:20]2[CH:28]=[N:27][N:26]([CH2:29][CH3:30])[C:21]2=[N:22][C:23]=1[CH2:24][CH3:25])=[O:15])=[O:10].[CH3:42][NH:43][CH2:44][CH2:45][OH:46].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][CH:40]=[CH:41][C:12]=3[NH:11][C:9](=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:43]([CH2:44][CH2:45][OH:46])[CH3:42])[C:19]([NH:31][CH:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)=[C:20]2[CH:28]=[N:27]1)[CH3:30]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-[(8-bromooctanoyl)amino]-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide (68 mg, 0.11 mmol, e.g. which can be as prepared in Intermediate 46) in N,N-dimethylformamide (5 ml) was treated with 2-(methylamino)ethanol (0.0175 ml, 0.22 mmol, commercially available e.g. from Aldrich) and N,N-diisopropylethylamine (0.038 ml, 0.22 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 (5 mg). LCMS showed MH+=622; TRET=2.15 min.

Workup

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

Sources & evidence

ORD record: ord-50149eb7cce2418f8c2eb1712b1fb97c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003663B2

Reaction notes

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