Acetic Acid → HCID 68752085, compound

HRID 1851258Notes

Reaction equation

HRID 1851258 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[NH:16][C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:10]=3[N:9]=2)[CH2:4][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[CH2:3][CH2:4][CH:5]([C:8]5[NH:16][C:11]6[CH:12]=[N:13][CH:14]=[CH:15][C:10]=6[N:9]=5)[CH2:6][CH2:7]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 68752438HCID 68752438, compoundHCID 866306554-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 68752085HCID 68752085, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

121 mg (0.6 mmol) 2-piperidine-4-yl-3H-imidazo[4,5-c]pyridine hydrochloride salt was dissolved in 3 mL methanol. 0.2 mL (1.2 mmol) Triethylamine in 3 mL DMF, 150 mg (0.5 mmol) 4-(6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde, 0.08 mL (1.3 mmol) acetic acid and 200 mg (1 mmol) NaBH(OAc)3 were added. The reaction mixture was stirred at room temperature and after 1 and 2 hours two additional portions of 2 equivalents NaBH(OAc)3 each were added. The solvent was removed by evaporation and the residue was purified by chromatography on silica gel (dichloromethane/methanol) to yield 126 mg of the desired product.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-1dd32a0164734439b7391d57d37b2f1e
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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