(Diethylamino)sulfur trifluoride → HCID 57867598, compound

HRID 1686078Notes

Reaction equation

HRID 1686078 reaction equation
[CH3:1][N:2]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C:3]1[C:8]([CH:9](O)[CH:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.CCN(S(F)(F)[F:36])CC>C(Cl)Cl>[F:36][CH:9]([C:8]1[C:3]([N:2]([CH3:1])[C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)[CH:10]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59706204HCID 59706204, compound

Product 1

HCID 57867598HCID 57867598, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{2-[methyl(pyridin-3-yl)amino]pyridin-3-yl}-2,2-dipyridin-3-ylethanol (31 mg) in 1.5 mL of CH2Cl2 was added DAST (20 mg). After 2 h stirring at room temperature, then reaction was cooled to 0 C and quenched with saturated aqueous sodium bicarbonate. then partitioned between saturated aqueous sodium bicarbonate and CH2Cl2. The aqueous solution was extracted with CH2Cl2 (2×), and the combined organic solutions were dried (Na2SO4) and purified by reverse phase HPLC to give 6 mg of 3-(1-fluoro-2,2-dipyridin-3-ylethyl)-N-methyl-N-pyridin-3-ylpyridin-2-amine. 1H NMR (CDCl3) δ 8.48 (2H, t, J=4.9 Hz), 8.45 (1H, dd, J=4.9, 2.0 Hz), 8.33 (2H, d, 20.5 Hz), 8.22 (1H, d, J=3.9 Hz), 8.12 (1H, s), 7.55 (1H, dd, J=7.8, 1.7 Hz), 7.49 (1H, d, J=8.1 Hz), 7.46 (1H, dd, J=8.1, 1.7 Hz), 7.23-7.11 (4H, m), 7.02-7.00 (1H, m), 6.10 (1H, dd, J=46.4, 4.1 Hz), 4.32 (1H, dd, J=26.4, 5.1 Hz), 3.28 (3H, s).

Workup

  1. customreaction
  2. temperaturewas cooled to 0 C
  3. customquenched with saturated aqueous sodium bicarbonate
  4. customthen partitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  5. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
  6. dry with materialthe combined organic solutions were dried (Na2SO4)
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-bed9c4c1c1824712bacd8ae383524713
Source dataset
uspto-grants-2012_04
Patent number
US08148535B2

Reaction notes

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