Acetic Acid → HCID 178424059, compound

HRID 1051335Notes

Reaction equation

HRID 1051335 reaction equation
[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][CH:14]=[N: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.[CH3:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]2[NH:44][N:43]=[C:42]([CH:45]3[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[N:41]=2)=[N:38][CH:39]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(Cl)(Cl)Cl>[CH3:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]2[NH:41][C:42]([CH:45]3[CH2:50][CH2:49][N:48]([CH2:20][C:19]4[CH:18]=[CH:17][C:16]([C:8]5[N:9]=[C:10]6[N:15]=[CH:14][CH:13]=[CH:12][N:11]6[C:7]=5[C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[CH:23][CH:22]=4)[CH2:47][CH2:46]3)=[N:43][N:44]=2)=[N:38][CH:39]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86631773HCID 86631773, compoundHCID 178423938HCID 178423938, compound2×

Product 1

HCID 178424059HCID 178424059, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.110 g (0.367 mM) 4-(3-phenylimidazo[1,2-a]pyrimidin-2-yl)benzaldehyde in 3 mL of THF is added triethylamine (2 eq). The reaction mixture is stirred for 5 minutes. To this solution is added 5-methyl-2-[3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl]pyridine dihydrochloride (Intermediate D) (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-50941b8ea39a4355975c15122c3812fd
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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