Acetic Acid → HCID 178509994, compound

HRID 1051343Notes

Reaction equation

HRID 1051343 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.[C:33]1([C:39]2[NH:43][N:42]=[C:41]([CH:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)[N:40]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(Cl)(Cl)Cl>[C:20]1([C:19]2[N:12]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]#[N:18])[C:11]3=[N:10][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([CH2:1][N:47]3[CH2:46][CH2:45][CH:44]([C:41]4[NH:40][C:39]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[N:43][N:42]=4)[CH2:49][CH2:48]3)=[CH:8][CH:7]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86631785HCID 86631785, compoundHCID 178420140HCID 178420140, compound2×

Product 1

HCID 178509994HCID 178509994, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.250 g (0.838 mM) of 2-(4-formylphenyl)-3-phenylimidazo[1,2-a]pyridine-8-carbonitrile in 6 mL of THF is added triethylamine (2 eq). The reaction mixture is stirred for 5 minutes. To this solution is added 4-(5-phenyl-1H-1,2,4-triazol-3-yl) piperidine (Intermediate M) (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-9dd50ece4fcc409f890e7b983a1059a0
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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