Benzophenone imine → HCID 59651108, compound

HRID 2426807Notes

Reaction equation

HRID 2426807 reaction equation
[NH2:1][CH:2]([C:4]1[O:8][C:7]([C:9]2[CH:14]=[C:13]([N:15]([CH3:21])[CH2:16][CH:17]3[CH2:19][CH:18]3[CH3:20])[N:12]=[C:11]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[CH:10]=2)=[N:6][N:5]=1)[CH3:3].[C:28](=N)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl.O.CCOC(C)=O>[C:29]1([C:28](=[N:1][CH:2]([C:4]2[O:8][C:7]([C:9]3[CH:14]=[C:13]([N:15]([CH3:21])[CH2:16][CH:17]4[CH2:19][CH:18]4[CH3:20])[N:12]=[C:11]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])[CH:10]=3)=[N:6][N:5]=2)[CH3:3])[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 136809Benzophenone imine2×HCID 11516750HCID 11516750, compound

Product 1

HCID 59651108HCID 59651108, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-[5-(1-aminoethyl)-1,3,4-oxadiazol-2-yl]-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide (0.544 g, 1.26 mmol, example 22) in 10 mL CH2Cl2 was added benzophenone imine (0.25 mL, 1.51 mmol). A white precipitate appeared gradually through the course of the reaction. The reaction was allowed to proceed for 15 h, when a further aliquot of benzophenone imine was added (0.160 mL, 0.894 mmol). After a further 24 h, the reaction was diluted with H2O and EtOAc, and the layers were separated. The aqueous layer was washed with EtOAc(2×), the combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by normal phase chromatography (2->35% EtOAc/hexanes) to afford N-(4-(5-{1-[(diphenyl methylene)amino]ethyl}-1,3,4-oxadiazol-2-yl)-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N -methylmethanesulfonamide as a yellow foam. 1H NMR (CDCl3, 400 MHz) δ 7.63 (m, 4H), 7.54-7.50 (m, 4H), 7.48 (m, 2H), 7.05 (s, 1H), 6.99 (s, 1H), 4.95 (q, J=6.5 Hz, 1H), 3.52 (dd, J=14.3, 6.2 Hz, 1H), 3.38 (s, 3H), 3.34 (dd, J=14.3, 6.3 Hz, 1H), 3.14 (s, 3H), 3.12 (s, 3H), 1.67 (d, J=6.6 Hz, 3H), 1.01 (d, J=6.0 Hz, 3H), 0.74 (m, 1H), 0.65 (m, 1H), 0.40 (m, 1H), 0.25 (m, 1H); LCMS [M+H]+=559.

Workup

  1. customA white precipitate appeared gradually through the course of the reaction
  2. waitAfter a further 24 h
  3. customthe layers were separated
  4. washThe aqueous layer was washed with EtOAc(2×)
  5. washthe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by normal phase chromatography (2->35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-349890cc224f4170bd88d4065aaffd3f
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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