Acetic Acid → HCID 25262352, compound

HRID 383270Notes

Reaction equation

HRID 383270 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[N:16]4[CH:17]=[CH:18][C:19]([C:21]5[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=5)[CH:24]=O)=[CH:20][C:15]4=[N:14][CH:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl.CCOC(C)=O>[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([CH2:24][C:23]2[CH:22]=[C:21]([C:19]3[CH:18]=[CH:17][N:16]4[C:12]([C:8]5[CH:9]=[CH:10][CH:11]=[C:6]([N:1]6[CH:5]=[CH:4][CH:3]=[N:2]6)[CH:7]=5)=[CH:13][N:14]=[C:15]4[CH:20]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 25262649HCID 25262649, compound

Product 1

HCID 25262352HCID 25262352, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzaldehyde (Ex. 1.9) (1 eq, 0.110 mmol, 40 mg) in DCM (2 ml) is added methyl piperazine (2 eq, 0.220, 0.24 ml) and the reaction mixture is stirred at room temperature for 2 h. After this time sodium triacetoxyborohydride (1.5 eq, 0.165 mmol, 36.7 mg) and acetic acid (0.1 ml) are added to the reaction mixture and this is stirred for a further one hour. The reaction is diluted with EtOAc and the organic phase is washed with NaHCO3. The aqueous layer is further extracted with EtOAc. The combined organic layers are washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The reaction mixture is purified by flash column chromatography eluting with 8:2 DCM/MeOH to yield 7-[3-(4-methyl-piperazine-1-ylmethyl)-phenyl]-3-(3-pyrazol-1-yl-phenyl)-imidazo-[1,2-a]pyridine as a yellow solid; [M+H]+=449

Workup

  1. stirringthis is stirred for a further one hour
  2. washthe organic phase is washed with NaHCO3
  3. extractionThe aqueous layer is further extracted with EtOAc
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe reaction mixture is purified by flash column chromatography
  9. washeluting with 8:2 DCM/MeOH

Sources & evidence

ORD record
ord-88dfb9fcb38a40f99d3d40115062a6b1
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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