2-(Dimethylamino)ethanol → HCID 10341736, compound

HRID 751318Notes

Reaction equation

HRID 751318 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:10]1[CH:19]=[N:18][C:17]2[C:12](=[CH:13][C:14]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)=[N:23][N:22]4[CH2:32][CH2:33][CH2:34][C:21]=34)=[CH:15][CH:16]=2)[N:11]=1>CN(C=O)C.ClCCl>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:10]1[CH:19]=[N:18][C:17]2[C:12](=[CH:13][C:14]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)=[N:23][N:22]4[CH2:32][CH2:33][CH2:34][C:21]=34)=[CH:15][CH:16]=2)[N:11]=1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 10338650HCID 10338650, compound

Product 1

HCID 10341736HCID 10341736, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Combine of 2-dimethylaminoethanol (180 mg, 2 mmol) with of sodium hydride (48 mg, 2 mmol) in dry DMF (5 mL) at 0-5° C. Stir for 10 min, add 2-chloro-7-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoxaline (Example 83; 60 mg, 0.17 mmol) in DMF (5 mL). Stir the reaction mixture for an additional 1 h. Dilute the mixture with dichloromethane. Wash the organic solution with brine, dry over sodium sulfate, filter and evaporate. Purify the crude product by column chromatography on silica gel to give target compound 35 mg (51%) as white solid. MS (electrospray, m/z) 414.2 (M+1). 1H NMR (CD2Cl2) δ 8.4 (s, 1H), 7.85 (d, 8.8 Hz, 1H), 7.81 (d, 1.6 Hz, 1H), 7.56 (t, 8.0 Hz, 1H), 7.51 (dd, 8.8 Hz, 1.6 Hz, 1H), 7.43 (d, 8.0 Hz, 1H), 7.09 (d, 8.0 Hz, 1H), 4.59 (t, 6 Hz, 2H), 4.27 (t, 7.2 Hz, 2H), 3.13 (t, 7.2 Hz, 2H), 2.80 (t, 6 Hz, 2H), 2.73 (m, 2H), 2.42 (s, 3H), 2.34 (s, 3H).

Workup

  1. customat 0-5° C
  2. stirringStir the reaction mixture for an additional 1 h
  3. washWash the organic solution with brine
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. customevaporate
  7. customPurify the crude product by column chromatography on silica gel
  8. customto give

Sources & evidence

ORD record
ord-cd2cd4b2a310445984b5440598b2c01d
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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