Acetic Acid → HCID 178509995, compound

HRID 1051338Notes

Reaction equation

HRID 1051338 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[C:16]([C:17]#[N:18])=[CH:15][CH:14]=[CH:13][N:12]3[C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:5][CH:4]=1)=O.C(N(CC)CC)C.Cl.Cl.[O:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[C:40]1[NH:44][N:43]=[C:42]([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[N:41]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(Cl)(Cl)Cl>[O:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[C:40]1[NH:41][C:42]([CH:45]2[CH2:50][CH2:49][N:48]([CH2:1][C:3]3[CH:4]=[CH:5][C:6]([C:9]4[N:10]=[C:11]5[C:16]([C:17]#[N:18])=[CH:15][CH:14]=[CH:13][N:12]5[C:19]=4[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:7][CH:8]=3)[CH2:47][CH2:46]2)=[N:43][N:44]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86631785HCID 86631785, compoundHCID 178478557HCID 178478557, compound2×

Product 1

HCID 178509995HCID 178509995, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.180 g (0.557 mM) 2-(4-formylphenyl)-3-phenylimidazo[1,2-a]pyridine-8-carbonitrile 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-(furan-2-yl)-1H-1,2,4-triazol-3-yl]piperidine dihydrochloride (Intermediate H) (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 60 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-7cda1684149842ca88cea888c518ae89
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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