Acetonitrile → HCID 59470515, compound

HRID 452306Notes

Reaction equation

HRID 452306 reaction equation
Cl.[F:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.Cl.[N:28]1([C:33](=N)[NH2:34])C=CC=N1.C(#N)C>CN(C=O)C.O>[F:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:33](=[NH:28])[NH2:34])[CH2:14][CH2:13]2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 68518567HCID 68518567, compound

Product 1

HCID 59470515HCID 59470515, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-(3-fluoropropyl)phenyl)piperazine hydrochloride (50 mg, 0.22 mmol) and diisopropylethylamine (82 μL, 0.47 mmol) in DMF (1 mL) was added 1H-pyrazole-1-carboximidamide hydrochloride (36 mg, 0.25 mmol). After stirring at room temperature for 9 h, the reaction mixture was purified via HPLC using a Phenomenex Luna C-18 (2) column (10μ, 250×21.2 mm, gradient method 15-55% B over 40 min., where B=90% ACN in water using 0.1% TFA as a modifier and A=water using 0.1% TFA as a modifier) with a flow rate of 20 mL/min afforded 4-(4-(3-fluoropropyl)phenyl)piperazine-1-carboximidamide as a white solid (36 mg, 42% yield). 1H NMR (300 MHz, DMSO-d6): δ 7.53 (br s, 3H), 7.09 (d, 2H, J=8.6 Hz), 6.92 (d, 2H, J=8.6 Hz), 4.50 (t, 1H, J=6.0 Hz), 4.34 (t, 1H, J=6.0 Hz), 3.57 (dd, 4H, J=5.3, 4.8 Hz), 3.17 (dd, 4H, J=5.2, 4.9 Hz), 2.58 (dd, 2H, J=8.1, 6.4 Hz), 1.98-1.80 (m, 2H); 19F NMR (282.4 MHz, DMSO-d6): δ−217.97 (m, 1F); 13C NMR (150 MHz, DMSO-d6): δ 156.1, 148.5, 132.1, 128.8, 116.2, 83.6 (82.5), 47.8, 44.8, 31.7 (31.6), 29.7 (29.6); HRMS calcd. for C14H21FN4: 265.18230 found 265.18240.

Workup

  1. customthe reaction mixture was purified via HPLC
  2. customover 40 min.

Sources & evidence

ORD record
ord-dfc3f15c69124e65acc6531bf0efda34
Source dataset
uspto-grants-2013_07
Patent number
US08491868B2

Reaction notes

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