Water → HCID 178425485, compound

HRID 1644606Notes

Reaction equation

HRID 1644606 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:9]=[C:10]([CH:12]=[C:13]([C:15]3[NH:23][C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[N:16]=3)[CH:14]=2)[NH2:11])=[N:4][CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[Na+].[CH3:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.O>C(Cl)Cl.CO>[Cl:1][C:2]1[C:3]([C:8]2[CH:9]=[C:10]([CH:12]=[C:13]([C:15]3[NH:23][C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[N:16]=3)[CH:14]=2)[NH:11][CH2:29][C:30]2[CH:37]=[CH:36][C:33]([CH3:34])=[CH:32][CH:31]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 517045Sodium AcetateHCID 178507329HCID 178507329, compound

Product 1

HCID 178425485HCID 178425485, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

NaCNBH4 (15.5 mg, 0.25 mmol) was added to a solution of Example 183 (32.1 mg, 0.1 mmol) in CH2Cl2-MeOH (2 mL) containing sodium acetate (12.3 mg, 0.15 mmol) and p-methyl benzaldehyde (14.4 mg, 0.12 mmol) at 0° C. The resulting suspension was stirred overnight and water (50 mL) was slowly added and the mixture extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting material was purified by LCMS (acetonitrile-water gradient) to give the title compound (20 mg, 45%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 2.27 (s, 3H) 4.3 (s, 2H) 7.01 (t, J=5.21 Hz, 1 H) 7.08 (d, J=5.11 Hz, 2 H) 7.13 (dd, J=7.21, 4.42, Hz, 1 H) 7.25 (dd, J=5.27, 3.48 Hz, 1 H) 7.39 (t, J=5.11 Hz, 1 H) 7.46 (t, J=5.11 Hz, 1 H) 7.58 (d, J=5.11 Hz, 2 H) 7.68 (dd, J=9.21, 5.42, Hz, 1 H) 8.76 (d, J=5.91 Hz, 1 H) 8.82 (d, J=5.91 Hz, 1 H). MS (ES) [M+H] calculated for C25H21ClN5, 426.14; found 426.09.

Workup

  1. extractionthe mixture extracted with CH2Cl2 (3×50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting material was purified by LCMS (acetonitrile-water gradient)

Sources & evidence

ORD record
ord-127afdd89c384b879f405b81bfd792bb
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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