Acetic Acid → HCID 25261430, compound

HRID 383277Notes

Reaction equation

HRID 383277 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[N:15]3[CH:16]=[CH:17][C:18]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[CH:23]=O)=[CH:19][C:14]3=[N:13][CH:12]=2)[CH:8]=[C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:6]=1)([CH3:3])[CH3:2].[CH2:34]([NH2:36])[CH3:35].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(Cl)Cl>[CH2:34]([NH:36][CH2:23][C:22]1[CH:21]=[C:20]([C:18]2[CH:17]=[CH:16][N:15]3[C:11]([C:9]4[CH:8]=[C:7]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:6]=[C:5]([NH:4][CH:1]([CH3:2])[CH3:3])[CH:10]=4)=[CH:12][N:13]=[C:14]3[CH:19]=2)[CH:27]=[CH:26][CH:25]=1)[CH3:35]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5049666Sodium triacetoxyborohydrideHCID 25261427HCID 25261427, compound

Product 1

HCID 25261430HCID 25261430, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-(2-isopropylamino-6-phenyl-pyridin-4-yl)-imidazo[1,2-a]pyridin-7-yl]-benzaldehyde (Ex. 1.186) (1 eq, 0.055 mmol, 30 mg) in MeOH (2 ml) is added ethyl amine (10 eq, 0.55, 0.27 ml) and acetic acid (2 eq, 0.11 mmol, 6.59 mg) and the reaction mixture is stirred at room temperature for 30 min. After this time sodium triacetoxyborohydride (5 eq, 0.27 mmol, 58.2 mg) is added to the reaction mixture and is stirred for a further 2 h. The reaction is diluted with CH2Cl2 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 {4-[7-(3-ethylaminomethyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-6-phenyl-pyridin-2-yl}-isopropyl-amine as a light yellow solid; [M+H]+=462

Workup

  1. stirringis stirred for a further 2 h
  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-aa92c1a92b464bbe8ca5ef3f24e1bf90
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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