Acetic Acid → HCID 178509996, compound

HRID 1051336Notes

Reaction equation

HRID 1051336 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.[Cl:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[NH:46][N:45]=[C:44]([CH:47]3[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]3)[N:43]=2)=[N:40][CH:41]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(Cl)(Cl)Cl>[Cl:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[NH:46][N:45]=[C:44]([CH:47]3[CH2:52][CH2:51][N:50]([CH2:1][C:3]4[CH:8]=[CH:7][C:6]([C:9]5[N:10]=[C:11]6[C:16]([C:17]#[N:18])=[CH:15][CH:14]=[CH:13][N:12]6[C:19]=5[C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:5][CH:4]=4)[CH2:49][CH2:48]3)[N:43]=2)=[N:40][CH:41]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86631785HCID 86631785, compoundHCID 178478574HCID 178478574, compound2×

Product 1

HCID 178509996HCID 178509996, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.230 g (0.712 mM) of 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 5-chloro-2-[3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl]pyridine dihydrochloride (Intermediate E) (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-6b0982f1a9b94a789396a8b02e7cfc7f
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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