Acetic Acid → HCID 178420111, compound

HRID 1674676Notes

Reaction equation

HRID 1674676 reaction equation
[C:1]1([C:7]2[C:8]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=3)=[N:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[NH:42]1[CH2:47][CH2:46][CH:45]([C:48]2[N:52]=[C:51]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=3)[NH:50][N:49]=2)[CH2:44][CH2:43]1.C(N(CC)CC)C.C(O)(=O)C>CN(C=O)C>[C:1]1([C:7]2[C:8]([C:19]3[CH:26]=[CH:25][C:22]([CH2:23][N:42]4[CH2:47][CH2:46][CH:45]([C:48]5[N:52]=[C:51]([C:53]6[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=6)[NH:50][N:49]=5)[CH2:44][CH2:43]4)=[CH:21][CH:20]=3)=[N:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 591643624-(5-Phenyl-2-pyridin-2-ylpyrimidin-4-yl)benzaldehydeHCID 178477979HCID 178477979, compound

Product 1

HCID 178420111HCID 178420111, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5-Phenyl-2-pyridin-2-ylpyrimidin-4-yl)benzaldehyde (4-3; 0.011 g, 0.033 mmol), sodium triacetoxyborohydride (0.010 g, 0.049 mmol) and 2-(3-piperidin-4-yl-1H-1,2,4-triazol-5-yl)pyridine hydrochloride (0.022 g, 0.082 mmol) were stirred in 0.5 ml of anhydrous DMF. Triethylamine (0.014 ml, 0.098 mmol) and acetic acid (0.007 ml, 0.13 mmol) were added and the reaction was stirred at ambient temperature for 6 h. The reaction was quenched by the addition of 3 drops of water and the resulting solution was purified by reverse phase preparative chromatography. This afforded 5-phenyl-2-pyridin-2-yl-4-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)pyrimidine (4-4) as a trifluoroacetic acid salt. 1H NMR (CDCl3): δ 9.12 (s, 1H), 9.09 (d, 1H), 8.94 (d, 1H), 8.72 (d, 2H), 8.20 (m, 1H), 8.15 (m, 2H), 7.98 (s, 1H), 7.75 (d, 2H), 7.58 (m, 3H), 7.43 (m, 2H), 7.36 (m, 2H), 4.40 (s, 2H), 3.62 (m, 2H), 3.25 (m, 2H), 2.42 (m, 2H), 2.12 (m, 2H). m/z (m+1): 551.2

Workup

  1. customThe reaction was quenched by the addition of 3 drops of water
  2. customthe resulting solution was purified by reverse phase preparative chromatography

Sources & evidence

ORD record
ord-63be0061d0de4e5f92e5386509ee9091
Source dataset
uspto-grants-2011_08
Patent number
US08003643B2

Reaction notes

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