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Structure of 1544-75-8

Chemical Structure| 1544-75-8

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Product Details of [ 1544-75-8 ]

CAS No. :1544-75-8
Formula : C7H5FN2O
M.W : 152.13
SMILES Code : O=C1NC2=CC=C(F)C=C2N1
MDL No. :MFCD05663528
InChI Key :DZRTZDURJKZGSP-UHFFFAOYSA-N
Pubchem ID :10329453

Safety of [ 1544-75-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 1544-75-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 38.88
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

48.65 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.2
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.22
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.42
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.27
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.59
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.54

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.16
Solubility 1.06 mg/ml ; 0.00696 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.84
Solubility 2.2 mg/ml ; 0.0145 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.08
Solubility 0.127 mg/ml ; 0.000832 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.36 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.75

Application In Synthesis of [ 1544-75-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1544-75-8 ]

[ 1544-75-8 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 75-44-5 ]
  • [ 367-31-7 ]
  • [ 1544-75-8 ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydrogen sulfide; In 1-methyl-pyrrolidin-2-one; at 90℃; under 22502.3 Torr; for 24h; General procedure: Add in a 15ml Teflon-lined reactor216 mg (2 mmol) of o-phenylenediamine, 56 mg (1 mmol)NaHS (molar ratio of o-phenylenediamine to NaHS is 1:2),Add 1 mL of NMP as the reaction solvent.Put the magnets and tighten the reactor.Then charge 3MPa of carbon dioxide,The reaction was stirred at 90 C for 24 hours.After cooling the reactor to room temperature,Extracted with ethyl acetate,Washed with saturated saline,After drying the organic layer, the solvent is removed under reduced pressure to give a crude material;The crude product is separated by recrystallization or column chromatography (200-300 mesh silica gel,Petroleum ether and ethyl acetate as eluent)99% white powder benzimidazolone 116mg,The yield was 88%.
(4) 3-(2-(benzoxazyl))-6-fluorobenzimidazol-2-(1H)-one; (Compound 14); mp: 295-296 C.
(10) 3-(2-(7-fluorobenzoxazyl))-5-fluorobenzimidazol-2-(1H)-one; (Compound 18); mp: 268-270 C.
(5) 3-(2-(6-fluorobenzoxazyl))-6-fluorobenzimidazol-2-(1H)-one; (Compound: 4); mp 284-285 C.
(9) 3-(2-(7-fluorobenzoxazyl))-6-fluorobenzimidazol-2-(1H)-one; (Compound 3); mp: 284-285 C.

  • 3
  • [ 615-18-9 ]
  • [ 1544-75-8 ]
  • 1-benzooxazol-2-yl-6-fluoro-1,3-dihydro-benzoimidazol-2-one [ No CAS ]
  • 1-benzooxazol-2-yl-5-fluoro-1,3-dihydro-benzoimidazol-2-one [ No CAS ]
  • 4
  • [ 1544-75-8 ]
  • 2-chloro-6-fluoro-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% b) A solution of <strong>[1544-75-8]5-fluoro-1H-benzo[d]imidazol-2(3H)-one</strong> (1.25 g, 8.22 mmol) in phosphorus oxychloride (25.2 ml, 270.34 mmol) was heated for 18 hours at 100 C. The reaction mixture was cooled to RT and excess of POCl3 was evaporated in vacuo. The residue was neutralized with saturated NaHCO3 solution (10 ml) and extracted with EtOAc (3×20 ml). The organic phase was washed with brine and then dried over MgSO4, filtered and concentrated under reduced pressure to afford 2-chloro-6-fluoro-1H-benzo[d]imidazole (1.146 g, 82%); 1H NMR (400 MHz, DMSO-d6) 7.09 (1H, ddd), 7.36 (1H, dd), 7.53 (1H, dd); m/z: (ES+) MH+, 171.34.
  • 5
  • [ 367-31-7 ]
  • [ 530-62-1 ]
  • [ 1544-75-8 ]
YieldReaction ConditionsOperation in experiment
88% In tetrahydrofuran; at 20℃;Inert atmosphere; Cooling with ice; A stirred solution of 4-fluorobenzene-1 ,2-diamine (15.1 g, 120 mmol) in THF (120 mL) under nitrogen was cooled using an ice-bath and then was treated with di(1 -/-imidazol-1 - yl)methanone (23.4 g, 144 mmol) portion-wise over 15 min. The resulting mixture was slowly warmed to room temperature then was concentrated in vacuo after 2.5 h. The residue was suspended in a mixture of water and DCM (250 mL each) and filtered off. This residue was then washed with water (50 mL) and DCM (50 mL), before being dried at 40 C under vacuum for 16 h to give the title compound (16.0 g, 105 mmol, 88%) as a brown solid. LCMS (high pH): Rt 0.57 min; [M-H+]" = 151.1 deltaEta NMR (400 MHz, DMSO-d6) ppm 10.73 (br s, 1 H), 10.61 (br s, 1 H), 6.91-6.84 (m, 1 H), 6.78-6.70 (m, 2H).
78% In tetrahydrofuran; at 150℃; for 0.333333h;Microwave irradiation; Intermediate 15: 5-Fluoro-1 ,3-dihvdro-2H-benzimidazol-2-one; A mixture of 4-fluoro-1 ,2-diaminobenzene (commercially available, 1.0 g, 7.9 mmol), carbonyldiimidazole (1.4 g) and THF (4 ml) was heated to 150 0C in a microwave reactor and stirred for 10 minutes. The mixture was heated to 150 0C and stirred for a further 10 <n="38"/>minutes. The mixture was cooled to room temperature and concentrated under vacuum. The residue was suspended in dilute hydrochloric acid and filtered. The filter-cake was washed with water and cyclohexane then dried under vacuum to give the title compound as a dark grey solid (0.95 g, 78%). 1 H-NMR (400 MHz, DMSO-d6): delta 10.73 (1 H, br s), 10.62 (1 H, br s), 6.87 (1 H, dd, J 8.5, 5 Hz), 6.78-6.70 (2H, m). UPLC-MS: 0.47 min, m/z 153 [M+H]+.
52% In tetrahydrofuran; at 20℃; a) 4-Fluorobenzene-1,2-diamine (2 g, 15.86 mmol) was dissolved in THF (49.4 ml) and 1,1'-Carbonyldiimidazole (2.83 g, 17.44 mmol) was added at RT. The reaction mixture was stirred overnight at RT. To this was added concentrated ammonia solution (1.5 ml) and the mixture stirred for 30 minutes and then diluted with water (100 ml). The resultant solid was collected by filtration, washed with water, followed by Et2O and then dried in vacuo to afford 5-fluoro-1H-benzo[d]imidazol-2(3H)-one (1.250 g, 52%); 1H NMR (400 MHz, DMSO-d6) 6.66-6.79 (2H, m), 6.81-6.94 (1H, m), 10.64 (1H, s), 10.76 (1H, s); m/z: (ES+) MH+, 151.19.
  • 6
  • [ 1544-75-8 ]
  • 6-fluoro-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1<i>H</i>-benzoimidazole [ No CAS ]
  • 7
  • [ 1544-75-8 ]
  • 2-chloro-5-fluoro-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With trichlorophosphate; at 100℃; for 18h; 10279] A solution of 5-fluoro- 1 ,3-dihydro-2H-benzo[d] imidazol-2-one 2b (1.562 g, 10.3 mmol) in phosphorus oxychloride (14 mE, 154.5 mmol) was heated for 18 hours at 100 C. The reaction mixture was cooled to room temperature and excess of P0C13 was evaporated in vacuo. The residue was neutralized with saturated NaHCO3 solution (10 mE) and extracted with EtOAc (3x20 mE). The organic phase was washed with brine and then dried over Mg504, filtered, and concentrated under reduced pressure to afford 2-chloro-6-fluoro-l H-benzo[d]imidazole 3b (1.552 g, 88%). ?H NMR (400 MHz, DMSO-d5) oe 7.51 (s, 1H), 7.34 (d, J=7.6 Hz, 1H), 7.08 (m, 1H); MS (ESI): mlz 171.0 [M+l]
Intermediate 14: 2-Chloro-5-fluoro-1 H-benzimidazole; A mixture of 5-fluoro-1 ,3-dihydro-2H-benzimidazol-2-one (Intermediate 15, 0.75 g, 4.1 mmol) and phosphorus oxychloride (2.1 ml) was heated to 110 0C and stirred for 5 hours.The mixture was cooled to room temperature and quenched by addition of ice. The mixture was left to stand 30 minutes, then basified to pH 9 with aqueous ammonium hydroxide solution. The resulting precipitate was filtered off, washed with water and dried under vacuum. The residue was dissolved in ethyl acetate, and filtered. The filtrate was concentrated under vacuum to give the title compound (0.49 g). 1 H-NMR (400 MHz,DMSO-d6): delta 7.52 (1 H, dd, J 9, 5 Hz), 7.35 (1 H, dd, J 9, 2.5 Hz) and 7.08 (1 H, ddd, J 10,9, 2.5 Hz). UPLC-MS: 0.55 min, m/z 171 [M+H]+.(Alternatively, 5-fluoro-2-chloro-1 H-benzimidazole is commercially available)
  • 9
  • [ 1544-75-8 ]
  • [ 1352227-31-6 ]
  • 10
  • [ 1544-75-8 ]
  • [ 1352227-05-4 ]
  • [ 1352227-08-7 ]
  • [ 1352227-06-5 ]
  • [ 1352227-07-6 ]
  • 11
  • [ 1544-75-8 ]
  • [ 1352227-09-8 ]
  • [ 1352227-12-3 ]
  • [ 1352227-10-1 ]
  • [ 1352227-11-2 ]
  • 12
  • [ 124-38-9 ]
  • [ 367-31-7 ]
  • [ 1544-75-8 ]
YieldReaction ConditionsOperation in experiment
87%Chromat. With tetrabutylammonium tungstate; In 1-methyl-pyrrolidin-2-one; at 140℃; under 760.051 Torr; for 24h;Schlenk technique;Catalytic behavior; General procedure: A typical procedure for the I-catalyzed reaction of aryl diamines with 1 atm CO2 was as follows: diamine (1 mmol), I (0.15 mmol), and N-methylpyrrolidone (NMP) (1 mL) were charged in a Schlenk tube with a magnetic stir bar. CO2 (1 atm) was introduced by a balloon, and the reaction mixture was stirred at 140 C for 24 h. The reaction solution was periodically analyzed by GC, LC, GC-MS, or NMR. A Teflon vessel placed in a stainless steel autoclave was used for reactions with CO2 at 20 atm.
  • 13
  • [ 1544-75-8 ]
  • [ 74-88-4 ]
  • 5-fluoro-1,3-dimethyl-1,3-dihydro-2H-benzimidazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; [00312] lodomethane (0.82 mL, 13.15 mmol) was added to a mixture of <strong>[1544-75-8]5-fluoro-1,3-dihydro-2H-benzimidazol-2-one</strong> (500. mg, 3.29 mmol) and potassium carbonate (1.81 g, 13.15mmol) in DMF (25 mL), and the reaction mixture stirred at ambient temperature for 16 h. DCM(30 mL) and water (60 mL) were added and the mixture stirred for 5 min. The DCM layer wasisolated by passing through a hydrophobic frit and the aqueous washed with DCM (2 x 50mL). The combined DCM extracts were concentrated under reduced pressure to yield 5-fluoro-1,3-dimethyl-benzimidazol-2-one (556 mg, 2.99 mmol, 91%).[00313] 1H NMR (300MHz, CDCI3) 5 = 6.91 - 6.71 (m, 3H), 3.42 (s, 3H), 3.41 (s, 3H)
81% A solution of 5-fluoro-1 H-benzo[d]imidazol-2(3H)-one (16.0 g, 105 mmol) in DMF (400 mL) under nitrogen was cooled with an ice-bath, using a mechanical stirrer for agitation. It was then treated over 10 min with sodium hydride (60% w/w in mineral oil, 13.1 g, 327 mmol) and the resulting mixture was stirred at this temperature for 30 min before being treated with iodomethane (26.3 mL, 422 mmol) over 30 min. The resulting mixture was then allowed to warm to room temperature and after 1 h was carefully treated with water (500 mL). The aqueous phase was extracted with EtOAc (3 x 800 mL) and the combined organics were washed with brine (1 L), dried over MgS04 and concentrated in vacuo. Purification of the brown residue by flash chromatography on silica gel (SP4, 1.5 kg column, gradient: 0 to 25% (3: 1 EtOAc/EtOH) in cyclohexane) gave the title compound (15.4 g, 86 mmol, 81 %) as a pink solid. LCMS (high pH): Rt 0.76 min; [M+H+]+ = 181.1 deltaEta NMR (400 MHz, CDCI3) ppm 6.86-6.76 (m, 2H), 6.71 (dd, J = 8.3, 2.3 Hz, 1 H), 3.39 (s, 3H), 3.38 (s, 3H).
  • 14
  • [ 1202680-24-7 ]
  • [ 367-31-7 ]
  • [ 1544-75-8 ]
YieldReaction ConditionsOperation in experiment
70% In toluene; for 29h;Reflux; Green chemistry; General procedure: A mixture of 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one (2a, 1.2 equiv), compounds 4 (1 equiv), and toluene (10 mL)was stirred at reflux conditions until amide intermediate wasconsumed (monitored by TLC). After cooling to r.t., the resultingprecipitate was filtered off and the solvent was evaporatedunder reduced pressure. The residue was transferred to anopen-bed silica gel column (3 × 7 cm). The column was elutedwith n-hexane-THF (1:2, v/v). Fractions containing compounds5 were combined and evaporated under reduced pressure togive compounds 5.
  • 15
  • [ 319-03-9 ]
  • [ 1544-75-8 ]
YieldReaction ConditionsOperation in experiment
50% With trimethylsilylazide; In tetrahydrofuran; for 30h;Reflux; General procedure: To a solution of phthalic anhydride in THF (1.0 mm), TMSA (4.0 equiv.) was added and the mixture was refluxed with stirring for 30 h. The resulting solution was concentrated in vacuo until a solid formed. The solid was washed with diethyl ether (5×4 ml) to obtain high purity imidazolin-2-ones 3.
  • 16
  • [ 50-00-0 ]
  • [ 1544-75-8 ]
  • [ 828911-01-9 ]
  • N-benzyl-2-{4-[(5-fluoro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl]piperazin-1-yl}acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.1% In ethanol; at 20℃; for 15h; Obtained through a method the N- acetyl benzylamine piperazine (II) intermediate (19. 6mmol), an alcoholic solution of formaldehyde (16. 3mmol), 5- fluoro-1,3-dihydro-benzimidazol-2-one (16. 3mmol) into 30ml of absolute ethanol, at room temperature for 15h. The reaction was concentrated under reduced pressure to give a crude oil. The crude product was purified by silica gel column chromatography to obtain the free base of N- benzyl-2- {4 - [(5-fluoro-2-oxo-2,3-dihydro-benzo -111- [(1] imidazol-1 yl) methyl] piperazin-1-yl} acetamide (V_19), 4.67g, yield 72.1%.
  • 17
  • [ 1544-75-8 ]
  • [ 828911-01-9 ]
  • N-benzyl-2-{4-[(5-fluoro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl]piperazin-1-yl}acetamide hydrochloride [ No CAS ]
  • 18
  • [ 1544-75-8 ]
  • C11H9FN2O5 [ No CAS ]
  • 19
  • [ 1544-75-8 ]
  • C45H45FN6O7 [ No CAS ]
  • 20
  • [ 1544-75-8 ]
  • C45H41F5N6O7 [ No CAS ]
  • 21
  • [ 1544-75-8 ]
  • [ 5292-43-3 ]
  • di-tert-butyl 2,2'-(5-fluoro-2-oxo-1H-benzo[d]imidazole-1,3(2H)-diyl)diacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
370 mg With caesium carbonate; In acetone; at 65℃; for 6h;Sealed tube; Step 1. A mixture of 5-fluoro-lH-benzo[d]imidazol-2(3H)-one (200 mg, 1.26 mmol), cesium carbonate (905 mg, 2.78 mmol) and tert-butyl 2-bromoacetate (0.39 mL, 2.65 mmol) in acetone (10 mL) was sealed and heated in an oil bath at 65 C for 6 h. The reaction mixture was filtered and concentrated in vacuo, and the residual oil taken up into DCM (5 mL) and purified by FCC (40 g silica gel, eluted with gradient 10-50% EtOAc-Hexanes) to afford di-tert-butyl 2,2'-(5-fluoro2-oxo-lH-benzo[d]imidazole-l,3(2H)-diyl)diacetate (370 mg) as a white solid. LC-MS retention time = 1.31 min; m/z = 269.2 [M-2(t- Bu)+H]+. (Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7^m-particles; Solvent A = 100% Water/ 0.05% TFA; Solvent B = 100% Acetonitrile/0.05% TFA; Flow Rate = 0.8 mL/min. Start % B = 2; Final % B = 98; Gradient Time = 1.5 minutes; Wavelength = 220 nm).
  • 22
  • [ 50-00-0 ]
  • [ 1544-75-8 ]
  • N-benzyl-2-(piperazin-1-yl)acetamide dihydrochloride [ No CAS ]
  • C21H24FN5O2*2ClH [ No CAS ]
  • 23
  • [ 1544-75-8 ]
  • [ 401567-12-2 ]
  • 24
  • [ 1544-75-8 ]
  • C8H9FN4 [ No CAS ]
  • 25
  • [ 367-31-7 ]
  • [ 503-38-8 ]
  • [ 1544-75-8 ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h; [0278] To a solution of 4-fluorobenzene-1,2-diamine lb (1.39 g, 11.0 mmol) and triethylamine (3.26 mE, 23.2 mmol) in methylene chloride (20 mE) was added dropwise a solution of diphosgene (0.69 mE, 5.72 mmol) in methylene chloride (5 mE) at 0 to 5 C. The resulting suspension was stirred for 2 hours at room temperature and filtered. The collected white solid was washed with water and dried to give compound 2b (1.56 g, 93%). ?H NMR (400 MHz, DMSO-d5) oe 10.73 (s, 1H), 10.61 (s, 1H), 6.97-6.81 (m, 1H), 6.74 (m, 2H); MS (ESI): mlz 153.1 [M+1]
  • 26
  • [ 1544-75-8 ]
  • [ 1073558-68-5 ]
 

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