1-Isopropylpiperazine → HCID 59730370, compound

HRID 228219Notes

Reaction equation

HRID 228219 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=O.[CH:19]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([CH3:21])[CH3:20].[BH4-].[Na+]>CO>[CH:19]([N:22]1[CH2:27][CH2:26][N:25]([CH2:1][C:3]2[CH:18]=[CH:17][C:6]([O:7][C:8]3[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=3)=[CH:5][CH:4]=2)[CH2:24][CH2:23]1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 780131-IsopropylpiperazineHCID 4311764Sodium borohydrideHCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamide2×

Product 1

HCID 59730370HCID 59730370, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using a method similar to Example 334, using 6-(4-formyl-phenoxy)-nicotinamide (compound of example 332, step 1) (0.304 g, 1.26 mmol), 1-isopropyl-piperazine (0.161 g, 1.26 mmol), and sodium borohydride (0.108 g, 2.85 mmol) in methanol (12 mL) provides 0.158 g (32%) of the title compound as a white solid (chromatography solvent: ethyl acetate→7:3 ethyl acetate:methanol): high resolution mass spectrum (electrospray): m/z calc for C20H27N4O2 355.2134, found 355.2140; 1H NMR (methanol-d4): 8.67 (d, 1H, J=2.0 Hz), 8.30 (dd, 1H, J=2.4, 8.8 Hz), 7.48-7.43 (m, 2H), 7.18-7.13 (m, 2H), 7.04 (d, 1H, J=8.3 Hz), 3.56 (s, 2H), 2.79-2.52 (m, 9H), 1.13 (d, 6H, J=6.8 Hz).

Sources & evidence

ORD record
ord-c8dbf2ab9b0544c9b4eecfef2db7fabd
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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