2-(Methylamino)ethanol → HCID 24985304, compound

HRID 1675699Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 3-[(8-bromooctanoyl)amino]-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide (42 mg, 0.067 mmol, e.g. which can be as prepared in Intermediate 47) in N,N-dimethylformamide (3 ml) was treated with 2-(methylamino)ethanol (0.011 ml, 0.13 mmol, commercially available e.g. from Aldrich) and N,N-diisopropylethylamine (0.0235 ml, 0.13 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 (33 mg). LCMS showed MH+=622; TRET=2.21 min.

Workup

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

Sources & evidence

ORD record: ord-6363cf8f5fec4c4db68d53baf2b4d106
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003663B2

Reaction notes

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