2-Bromoethanol → HCID 73504288, compound

HRID 1478562Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

(S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyrimidin-2-yl)morpholine HCl salt 20 mg (0.04 mmol) was dissolved in dimethylformamide 1 ml, and 2-bromoethanol 6.6 mg (0.05 mmol) and K2CO3 15 mg (0.11 mmol) were added and then charged with nitrogen, followed by stirring at 60° C. for 4 hours. After the reaction, the reaction mixture was concentrated under reduced pressure to remove dimethylformamide, followed by extraction with EA and brine, and the organic layer was dried over MgSO4. Separation by column chromatography (methylene chloride:methanol=10:1) gave a product 33 mg (65%).

Workup

additioncharged with nitrogen
customAfter the reaction
concentrationthe reaction mixture was concentrated under reduced pressure
customto remove dimethylformamide
extractionfollowed by extraction with EA and brine
dry with materialthe organic layer was dried over MgSO4
customSeparation by column chromatography (methylene chloride:methanol=10:1)

Sources & evidence

ORD record: ord-0158c5c7fd0340949e8c2a5966dc761b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403831B2

Reaction notes

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