Acetic Acid → HCID 67028426, compound

HRID 1051342Notes

Reaction equation

HRID 1051342 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH:16]=[C:15]([C:17]#[N:18])[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.[NH:35]1[CH2:40][CH2:39][CH:38]([C:41]2[N:45]=[C:44]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=3)[O:43][N:42]=2)[CH2:37][CH2:36]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][C:15]([C:17]#[N:18])=[CH:16][C:11]3=[N:10][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([CH2:1][N:35]3[CH2:40][CH2:39][CH:38]([C:41]4[N:45]=[C:44]([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=5)[O:43][N:42]=4)[CH2:37][CH2:36]3)=[CH:8][CH:7]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67028021HCID 67028021, compound2×HCID 86631784HCID 86631784, compound

Product 1

HCID 67028426HCID 67028426, 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-7-carbonitrile 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)1,2,4-oxadiazol-5-yl]pyridine dihydrochloride (Intermediate L) (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-cc1b96c41e20450c9ad0b5d4c529f895
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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