Acetic Acid → HCID 178487433, compound

HRID 1441289Notes

Reaction equation

HRID 1441289 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[N:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:4]=1.[NH:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:33]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[NH:31][N:30]=2)[CH2:25][CH2:24]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[N:8]=[N:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH2:13][N:23]3[CH2:24][CH2:25][CH:26]([C:29]4[CH:33]=[C:32]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=5)[NH:31][N:30]=4)[CH2:27][CH2:28]3)=[CH:15][CH:16]=2)=[C:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 591643594-(6-Methoxy-4-phenylpyridazin-3-yl)benzaldehydeHCID 178420066HCID 178420066, compound

Product 1

HCID 178487433HCID 178487433, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(6-Methoxy-4-phenylpyridazin-3-yl)benzaldehyde (2-2; 80 mg, 0.27 mmol) was dissolved in dry dimethylformamide (2 mL) and 2-(3-piperidin-4-yl-1H-pyazol-5-yl)pyridine (1-4; 99 mg, 0.43 mmol) and acetic acid (0.14 mL, 2.3 mmol) were added. After stirring for 15 min., sodium triacetoxyborohydride (116 mg, 0.54 mmol) was added and the reaction mixture was stirred at ambient temperature for 12 hours. This reaction mixture was partially evaporated and the residue chromatographed on a silica gel column eluting with a 0-5% methanol/ethyl acetate sat'd with NH4OH. 3-methoxy-5-phenyl-6-(4-{[4-(5-pyridin-2-yl-1H-pyrazol-3-yl)piperidin-1-yl]methyl}phenyl)pyridazine (2-3) was obtained as a nearly pure viscous oil. NMR (CDCl3): δ8.60 (1H, d, J=5 Hz), 7.69-7.72 (2H, m), 7.23-7.35 (6H, m), 7.17 (2H, br d, J=7 Hz), 6.98 (1H, s), 6.61 (1H, s), 4.22 (3H, s), 3.52 (2H, s), 2.95 (2H, d, J=12 Hz), 2.72 (1H, m), 2.10 (2H, br t, J=1 Hz), 1.97 (2H, br d, J=12 Hz), 1.81 (2H, br q, J=11).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 12 hours
  2. customThis reaction mixture was partially evaporated
  3. customthe residue chromatographed on a silica gel column
  4. washeluting with a 0-5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-41f5dea5f2e341be991aade1b4c01063
Source dataset
uspto-grants-2010_02
Patent number
US07655649B2

Reaction notes

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