Acetic Acid → HCID 178420104, compound

HRID 1851254Notes

Reaction equation

HRID 1851254 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[NH:10][N:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[N:7]=2)[CH2:3]1.C(N(CC)CC)C.[C:24]1([C:30]2[C:31]([C:39]3[CH:46]=[CH:45][C:42]([CH:43]=O)=[CH:41][CH:40]=3)=[N:32][C:33]3[N:34]([CH:36]=[CH:37][N:38]=3)[CH:35]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.CN(C=O)C>[C:24]1([C:30]2[C:31]([C:39]3[CH:40]=[CH:41][C:42]([CH2:43][N:2]4[CH2:5][CH:4]([C:6]5[N:7]=[C:8]([C:11]6[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=6)[NH:9][N:10]=5)[CH2:3]4)=[CH:45][CH:46]=3)=[N:32][C:33]3[N:34]([CH:36]=[CH:37][N:38]=3)[CH:35]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 687522832-(5-Azetidine-3-yl-[1,2,4]triazol-3-yl)-pyridine hydrochloride saltHCID 866306554-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 178420104HCID 178420104, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

274 mg (1 mmol) 2-(5-azetidine-3-yl-[1,2,4]triazol-3-yl)-pyridine hydrochloride salt were dissolved in 5 mL methanol. After addition of 0.28 mL (2 mmol) triethylamine, 250 mg (0.84 mmol) 4-(6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde dissolved in 5 mL DMF, 0.13 mL (2.20 mmol) acetic acid and 356 mg (1.68 mmol) NaBH(OAc)3, the reaction mixture was stirred at room temperature. Two additional portions of 2 equivalents NaBH(OAc)3 each were added after 1.5 and 3 hours. After 4 hours the solvent was removed by evaporation. Evaporation was repeated after addition of toluene. The residue was purified by chromatography on silica gel (dichloromethane/methanol) to yield 291 mg of the desired product.

Workup

  1. customAfter 4 hours the solvent was removed by evaporation
  2. customEvaporation
  3. additionafter addition of toluene
  4. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-5f303b7b9d714370a2aa1dc34966d18e
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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