Acetic Anhydride → (2-Chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)methyl acetate

HRID 1963774Notes

Reaction equation

HRID 1963774 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:35][C:36](OC(C)=O)=[O:37]>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[C:36]([O:9][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:6]=1)(=[O:37])[CH3:35]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 44609230(2-Chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)methanol

Product 1

HCID 44609232(2-Chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)methyl acetate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(Some starting materials may be obtained from Adesis Inc., New Castle, Del.) A mixture of (2-chloro-5-(4-morpholinoquinolin-6-yl)pyridin-3-yl)methanol (63 mg, 177 μmol), Hunig's Base (300 μl, 1718 μmol), and Ac2O (17 μl, 177 μmol) in DCM (10 mL) was stirred at rt. A small amount of DMF (10 drops) was added. After 2 h, a tiny amount of DMAP was added. After an additional 1 h, the solvent was removed under vacuum and the residue was treated with water. The slurry was extracted with DCM containing MeOH (2%). The organic phase was dried over Na2SO4, concentrated, and purified on silica using 1% MeOH in DCM to give a film (70 mg). LCMS (ESI, pos. ion): calc'd for C21H20ClN3O3: 397.1; found: 398.1 (M+1). 1H NMR (400 MHz, TFA-CHLOROFORM-d) δ ppm 2.26 (s, 3 H) 3.97 (d, J=4.02 Hz, 4 H) 4.11 (d, J=4.52 Hz, 4 H) 5.39 (s, 2 H) 7.10 (d, J=7.03 Hz, 1 H) 8.10-8.19 (m, 1 H) 8.17-8.28 (m, 2 H) 8.33 (s, 1 H) 8.60 (d, J=6.52 Hz, 1 H) 8.91 (d, J=2.01 Hz, 1 H) 13.20 (s, 1 H)

Workup

  1. waitAfter an additional 1 h
  2. customthe solvent was removed under vacuum
  3. additionthe residue was treated with water
  4. extractionThe slurry was extracted with DCM
  5. additioncontaining MeOH (2%)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated
  8. custompurified on silica using 1% MeOH in DCM
  9. customto give a film (70 mg)

Sources & evidence

ORD record
ord-379ed385330f4b3487994ad8e51114d5
Source dataset
uspto-grants-2013_04
Patent number
US08415376B2

Reaction notes

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