Morpholine → LY2109761

HRID 915526Notes

Reaction equation

HRID 915526 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:26][CH2:27]OS(C)(=O)=O)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[N:33]1([CH2:27][CH2:26][O:25][C:21]2[CH:20]=[C:19]3[C:24]([C:15]([C:8]4[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)=[N:11][N:10]5[CH2:12][CH2:13][CH2:14][C:9]=45)=[CH:16][CH:17]=[N:18]3)=[CH:23][CH:22]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 58958827HCID 58958827, compound

Product 1

HCID 11655119LY2109761Yield 100%

Procedure

Heat methanesulfonic acid 2-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-ethyl ester (87 mg, 0.19 mmol) with morpholine (1 mL) at 50° C. for 4 hours. Remove the morpholine in vacuo and then extract the product with isopropyl alcohol:chloroform (1:3). Wash the organic layer with sodium chloride and dry over sodium sulfate. Concentrate in vacuo to give the desired title product as a slight yellow solid (83 mg, 100%). MS ES+ m/e 442.0 (M+1).

Workup

  1. customRemove the morpholine in vacuo
  2. extractionextract the product with isopropyl alcohol:chloroform (1:3)
  3. washWash the organic layer with sodium chloride
  4. dry with materialdry over sodium sulfate
  5. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-914820237cb24b179ce5590951d3a747
Source dataset
uspto-grants-2007_09
Patent number
US07265225B2

Reaction notes

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