2-Bromoethanol → HCID 118364830, compound

HRID 1478582Notes

Reaction equation

HRID 1478582 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C@H:20]4[O:25][CH2:24][CH2:23][N:22]([C:26]5[N:31]=[CH:30][C:29]([C:32]6[CH2:33][CH2:34][NH:35][CH2:36][CH:37]=6)=[CH:28][N:27]=5)[CH2:21]4)[N:17]=[N:18][C:13]3=[N:12][CH:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:45][CH2:46][OH:47].ClCCl.CO>CN(C=O)C.CCN(CC)CC>[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C@H:20]4[O:25][CH2:24][CH2:23][N:22]([C:26]5[N:27]=[CH:28][C:29]([C:32]6[CH2:33][CH2:34][N:35]([CH2:45][CH2:46][OH:47])[CH2:36][CH:37]=6)=[CH:30][N:31]=5)[CH2:21]4)[N:17]=[N:18][C:13]3=[N:12][CH:11]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 118364853HCID 118364853, compound

Product 1

HCID 118364830HCID 118364830, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6228DimethylformamideSolvent

Procedure

(S)-2-fluoro-5-(1-((4-(5-(1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)morpholine-2-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)benzonitrile 44 mg (0.09 mmol) was dissolved in DMF 1 ml. Potassium carbonate 36 mg (0.26 mmol) and 2-bromoethanol 0.009 ml (0.13 mmol) were added, and Et3N (2 drop) were added, followed by stirring at room temperature for 13 hours under nitrogen gas. When the reaction was completed, the reaction mixture was extracted two times or more with ethyl acetate and water, and concentrated under reduced pressure. PCL using 10% dichloromethane/methanol gave (S)-2-fluoro-5-(1-((4-(5-(1-(2-hydroxyethyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)morpholin-2-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)benzonitrile 9 mg (0.017 mmol) with a yield of 19%.

Workup

  1. extractionthe reaction mixture was extracted two times
  2. concentrationmore with ethyl acetate and water, and concentrated under reduced pressure

Sources & evidence

ORD record
ord-04218b62449e4c93897c46074287e142
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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