Acetic Acid → HCID 178420045, compound

HRID 2048159Notes

Reaction equation

HRID 2048159 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.[S:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38]1[NH:42][N:41]=[C:40]([CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[N:39]=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:46]3[CH2:47][CH2:48][CH:43]([C:40]4[NH:39][C:38]([C:34]5[S:33][CH:37]=[CH:36][CH:35]=5)=[N:42][N:41]=4)[CH2:44][CH2:45]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 178478559HCID 178478559, compound2×

Product 1

HCID 178420045HCID 178420045, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.120 g (0.402 mM) of 4-(3-phenylimidazo[1,2-a]pyridin-2-yl)benzaldehyde in 5 mL of THF is added triethylamine (2 eq). The reaction mixture is stirred for 5 minutes. To this solution is added 4-[5-(thiophen-2-yl)-1H-1,2,4-triazol-3-yl]piperidine dihydrochloride (Intermediate I) (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-3f7ab5658cc443a2bca1fb797b87853d
Source dataset
uspto-grants-2013_11
Patent number
US08592591B2

Reaction notes

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