Acetic Acid → HCID 67028131, compound

HRID 2048161Notes

Reaction equation

HRID 2048161 reaction equation
[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[C:16]2[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.Cl.[NH:33]1[CH2:38][CH2:37][CH:36]([C:39]2[CH:43]=[C:42]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)[NH:41][N:40]=2)[CH2:35][CH2:34]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(Cl)(Cl)Cl>[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[C:16]2[CH:23]=[CH:22][C:19]([CH2:20][N:33]3[CH2:34][CH2:35][CH:36]([C:39]4[NH:40][N:41]=[C:42]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=5)[CH:43]=4)[CH2:37][CH2:38]3)=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86631786HCID 86631786, compoundHCID 178478532HCID 178478532, compound2×

Product 1

HCID 67028131HCID 67028131, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.250 g (0.838 mM) of 4-(3-phenylimidazo[1,2-a]pyridin-2-yl)benzaldehyde in 6 mL of THF is added triethylamine (2 eq). The reaction mixture is stirred for 5 minutes. To this solution is added 2-[3-(piperidin-4-yl)-1H-pyrazol-5-yl]pyridine dihydrochloride (Intermediate K) (1.5 eq) followed by acetic acid (2.5 eq). The reaction mixture is stirred for 10 minutes. To this mixture is added NaBH(OAc)3 (6 eq) over a period of 40 minutes. The reaction mixture is stirred overnight. The reaction mixture is quenched with methanol and concentrated. The residue obtained is taken up in chloroform and washed with water, dried and concentrated. The crude is purified on a flash column chromatography to obtain the desired compound.

Workup

  1. stirringThe reaction mixture is stirred for 10 minutes
  2. stirringThe reaction mixture is stirred overnight
  3. customThe reaction mixture is quenched with methanol
  4. concentrationconcentrated
  5. customThe residue obtained
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe crude is purified on a flash column chromatography

Sources & evidence

ORD record
ord-37333cfbf078409f94ff80aef4f033d0
Source dataset
uspto-grants-2013_11
Patent number
US08592591B2

Reaction notes

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