Home Cart Sign in  
Chemical Structure| 6274-22-2 Chemical Structure| 6274-22-2

Structure of 6274-22-2

Chemical Structure| 6274-22-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 6274-22-2 ]

CAS No. :6274-22-2
Formula : C8H10N2O
M.W : 150.18
SMILES Code : CNC(=O)C1=CC=C(N)C=C1
MDL No. :MFCD00665792
Boiling Point : No data available
InChI Key :XAGFYNSCWICYPA-UHFFFAOYSA-N
Pubchem ID :235516

Safety of [ 6274-22-2 ]

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

Computational Chemistry of [ 6274-22-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 2.0
Molar Refractivity 43.84
TPSA ?

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

55.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.23
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

0.44
Log Po/w (WLOGP)?

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

0.64
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.

0.91
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

0.65
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.77

Water Solubility

Log S (ESOL):?

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

-1.32
Solubility 7.19 mg/ml ; 0.0479 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.17
Solubility 10.3 mg/ml ; 0.0683 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

-2.41
Solubility 0.588 mg/ml ; 0.00392 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

No
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.

-6.9 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

1.0 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)

1.0

Application In Synthesis of [ 6274-22-2 ]

* 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 [ 6274-22-2 ]

[ 6274-22-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 6274-22-2 ]
  • [ 121-60-8 ]
  • 4-[(<i>N</i>-acetyl-sulfanilyl)-amino]-benzoic acid methylamide [ No CAS ]
  • 2
  • [ 2585-23-1 ]
  • [ 6274-22-2 ]
YieldReaction ConditionsOperation in experiment
86% With water; ammonium chloride; zinc; In tetrahydrofuran; methanol; Synthesis of 4-Amino-N-methyl-benzamide Ammonium chloride (29.6 g, 55.4 mmol) in water (200 mL) and methanol (200 mL) was added to a solution of N-methyl-4-nitro-benzamide (10 g, 55.4 mmol) in THF (160 mL). Zinc powder (29 g, 44.4 mmol) was added portion wise and the mixture stirred for 15 minutes. The reaction mixture was filtered over celite, the filtrate was then concentrated and extracted with ethyl acetate. The organics were washed with brine solution, dried over Na2SO4 and concentrated to afford 7.2 g (86%) of 4-amino-N-methyl-benzamide. 1H NMR: (DMSO-d6): delta 7.9 (s, 1H), 7.6 (d, 2H), 6.5 (d, 2H), 5.6 (s, 2H), 2.7 (s, 3H).
84% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 1520.1 Torr; for 12h; (b) Preparation of intermediary compound 4-amino-iV-methylbenzamide:To a solution of 7V-methyl-4-nitrobenzamide (23.0 g, 127.8 mmol) in ethanol (460 rnL) was added palladium on carbon (Pd/C, 10%, 50% moistened, 15.0 g). The mixture was hydrogenated under 2.0 atmospheric pressure at room temperature for 12 hours. After completion of the reaction, the reaction mixture was filtered through Celite and thoroughly washed with ethanol. The filtrate was evaporated and the residue washed with diisopropyl ether to give 16.0 g (84 % yield) of 4-amino-N-methylbenzamide as an off-white solid. 1H-NMR (300 MHz, DMSOd6) delta 7.94 (bs, IH), 7.54 (d, J= 8.7 Hz, 2H), 6.52 (d, J= 8.7 Hz, 2H), 5.57 (s, 2H), 2.72 (d, J= 4.5 Hz, 3H). LC-MS 172.5 (M+Na).
67.4% With ethanol; tin(ll) chloride; at 20℃; Place 1.000g (5.54mmol) 24a and 5.000g (22.15mmol) stannous chloride in a 50ml eggplant-shaped bottle, add 20ml absolute ethanol to the eggplant-shaped bottle, and react at room temperature. After the reaction was completed, the solvent was evaporated, about 200 ml of ethyl acetate was added, the pH was adjusted to about 8 with saturated sodium bicarbonate solution, filtered, the aqueous layer was extracted three times with 20 ml of ethyl acetate, the organic layers were combined, and the acetic acid was washed with saturated sodium chloride solution The ethyl acetate layer was dried once with anhydrous sodium sulfate, filtered, and evaporated to dryness to obtain a white solid. The dichloromethane was purified by rapid preparative liquid phase: methanol = 100: 1) to obtain a white fluffy solid in a yield of 67.4%.
  • 3
  • [ 6274-22-2 ]
  • [ 14301-31-6 ]
  • [ 104775-50-0 ]
  • 4
  • [ 6274-22-2 ]
  • [ 145531-28-8 ]
  • N-methyl-4-<(3,6-diazido-9-acridinyl)amino>benzenecarboxamide hydrochloride [ No CAS ]
  • 6
  • [ 1719-57-9 ]
  • [ 2835-68-9 ]
  • [ 6274-22-2 ]
  • 7
  • [ 6274-22-2 ]
  • [ 100-52-7 ]
  • Sodium; (Z)-1-ethoxycarbonyl-2-methanesulfonyloxy-ethenolate [ No CAS ]
  • sodium; 4-methanesulfonyl-1-(4-methylcarbamoyl-phenyl)-2-oxo-5-phenyl-2,5-dihydro-1<i>H</i>-pyrrol-3-olate [ No CAS ]
  • 8
  • [ 6274-22-2 ]
  • [ 444723-30-2 ]
  • NU 6139 [ No CAS ]
  • 9
  • [ 6274-22-2 ]
  • N-methyl-4-<(3,6-diamino-9-acridinyl)amino>benzenecarboxamide dihydrochloride [ No CAS ]
  • 10
  • [ 122-04-3 ]
  • 5-oxymethyl-2-phenyl-oxazolidine [ No CAS ]
  • [ 6274-22-2 ]
  • 11
  • [ 6274-22-2 ]
  • 4-sulfanilylamino-benzoic acid methylamide [ No CAS ]
  • 13
  • [ 6274-22-2 ]
  • [ 1885-14-9 ]
  • [ 189269-44-1 ]
YieldReaction ConditionsOperation in experiment
87% With sodium carbonate; In tetrahydrofuran; water; ethyl acetate; at 0 - 20℃; General procedure: Into a stirringmixture of ethyl acetate (20 mL), tetrahydrofuran (4 mL), water(4 mL), sodium carbonate (0.8 g, 7.9 mmol, 0.6 equiv.), and 4-isopropoxyaniline (2.0 g, 13.2 mmol, 1 equiv.), phenyl chloroformate(2.3 g, 14.5 mmol, 1.1 equiv.) was added dropwise at 0 C.The reaction was stirred at room temperature overnight, then itwas evaporated under reduced pressure and the resultant wasadded into 20 mL water, the precipitate was filtered and washedwith water, then dried under vacuum to afford 3.2 g of 13a as whitesolid; yield: 90%.
With sodium hydroxide; In 1,4-dioxane; methanol; chloroform; (1) To a suspension of <strong>[6274-22-2]4-(methylcarbamoyl)aniline</strong> (1.0 g) in 1,4-dioxane (10 ml) were added 1N sodium hydroxide solution (13.4 ml) and phenyl chloroformate (1.26 g) under ice-cooling, and the mixture was stirred for 2 hours at ambient temperature. The reaction mixture was poured into water and extracted with a mixture of chloroform and methanol. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate to give phenyl 4-(methylcarbamoyl)phenylcarbamate (1.70 g) as pale yellow crystals. mp: 190-192 C., NMR (DMSO-d6, delta): 2.70 (1H, d, J=5 Hz), 2.77 (2H, d, J=5 Hz), 5.55 (0.6H, br s), 6.51 (0.9H, d, J=8 Hz), 6.71-6.80 (1.1H, m), 7.15 (0.8H, t, J=8 Hz), 7.20-7.31 (1.8H, m), 7.43 (1.2H, t, J=8 Hz), 7.50-7.60 (2H, m), 7.80 (1.2H, d, J=8 Hz), 7.92 (0.3H, br d, J=5 Hz), 8.31 (1H, br s), 9.30 (0.4H, s).
With sodium hydroxide; In 1,4-dioxane; water; at 20℃; for 2h; To a suspension of <strong>[6274-22-2]4-(methylcarbamoyl)aniline</strong> (1.0 g) in 1,4-dioxane (10 ml) were added 1N sodium hydroxide solution (13.4 ml) and phenyl chloroformate (1.26 g) under ice-cooling, and the mixture was stirred for 2 hours at ambient temperature. The reaction mixture was poured into water and extracted with a mixture of chloroform and methanol. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate to give phenyl 4-(methylcarbamoyl)phenylcarbamate (1.70 g) as pale yellow crystals. mp: 190-192 C. NMR (DMSO-d6, delta): 2.70 (1H, d, J=5 Hz), 2.77 (2H, d, J=5 Hz), 5.55 (0.6H, br s), 6.51 (0.9H, d, J=8 Hz), 6.71-6.80 (1.1H, m), 7.15 (0.8H, t, J=8 Hz), 7.20-7.31 (1.8H, m), 7.43 (1.2H, t, J=8 Hz), 7.50-7.60 (2H, m), 7.80 (1.2H, d, J=8 Hz), 7.92 (0.3H, br d, J=5 Hz), 8.31 (1H, br s), 9.30 (0.4H, s).
  • 14
  • [ 888500-54-7 ]
  • [ 6274-22-2 ]
  • N-methyl-4-[4-(3-trifluoromethyl-pyrazol-1-yl)-quinolin-2-ylamino]-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% In butan-1-ol; at 20 - 35℃; for 96h;Heating / reflux; Example 22Synthesis of N~Methyl-4-[4-(3-trifluoromethyl-pyrazol-l-yl)-quinolin-2-ylamino]- benzamide (E 22); E 22 EPO <DP n="143"/>4-Amino-N-methyl-benzamide (166 mg, 1.11 mmol) was added to a stirred solution of 2-chloro-4-(3-trifluoromethyl-pyrazol-l-yl)-quinoline (300 mg, 1.00 mmol) in 1-butanol (10 mL), under nitrogen, at room temperature. This reaction mixture was stirred under reflux for about 4 days and filtered while hot. The resulting pale brown solid was stirred in z-PrOH, filtered off, and dried to give the desired product (120 mg, 30%). Melting range: 250-252 0C1H NMR (400 MHz, DMSO) delta 10.02 (-NH, D2O exchangeable, IH), 8.28-8.27 (d, J=4.50 Hz, IH), 8.06 (d, J=8.59 Hz, 2H), 7.91-7.41 (m, 6H), 7.32 (s, IH), 7.19-7.18 (d, J=2.41 Hz, IH), 2.79 (s, 3H). IR (cm"1): 3203, 2690, 1667, 1608 MS (m/z): 412 (M+, 100%)
  • 15
  • [ 463-71-8 ]
  • [ 6274-22-2 ]
  • [ 767329-08-8 ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine; In tetrahydrofuran; at 0℃; for 1h; Thiophosgene (1.13 ml, 1.1 eq) is added dropwise to a solution cooled down to 0 C., of <strong>[6274-22-2]4-amino-N-methylbenzamide</strong> (2 g, 1 eq) and triethylamine (5.6 ml, 3 eq) in tetrahydofuran (260 ml). The mixture is stirred for 30 minutes at 0 C. then the cold bath is removed and stirring is continued for another 30 minutes. Water (100 ml) and diethyl ether (250 ml) are added to the mixture. After decantation and extractions, the organic phases are combined, washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40 C. The solid obtained is recrystallized from a dichloromethane/petroleum ether mixture (2.2 g; 86% yield). NMR (1H, 400 MHz, DMSO-d6): delta 2.77 (d, 3H), 7.51 (AB, 2H), 7.88 (AB, 2H), 8.52 (m, 1H).
  • 16
  • [ 24424-99-5 ]
  • [ 6274-22-2 ]
  • tert-butyl (4-(methylcarbamoyl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; ethyl acetate; (1) To a suspension of <strong>[6274-22-2]4-amino-N-methylbenzamide</strong> (500 mg) in tetrahydrofuran (5 ml) was added di-tert-butyl dicarbonate (799 mg) and the mixture was stirred for 18 hours at 50 C. The mixture was concentrated and the residue was dissolved in ethyl acetate. The solution was stirred under ice-cooling, and the resulting precipitates were collected by filtration to give N-(tert-butoxycarbonyl)-4-methylcarbamoylaniline (500 mg). mp: 185.2 C. NMR (CDCl3, delta): 1.54 (9H, s), 3.00 (3H, d, J=6 Hz), 6.12 (1H, br s), 6.69 (1H, br s), 7.43 (2H, d, J=9 Hz), 7.70 (2H, d, J=9 Hz),
  • 17
  • 8-[2,6-dichloro-3-(4-carboxymethyl-2,5-dioxopiperazin-1-yl)benzyloxy]-2-methylquinoline [ No CAS ]
  • [ 6274-22-2 ]
  • 8-[2,6-Dichloro-3-[4-[4-(methylcarbamoyl)phenylcarbamoylmethyl]-2,5-dioxopiperazin-1-yl]benzyloxy]-2-methylquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
(5) 8-[2,6-Dichloro-3-[4-[4-(methylcarbamoyl)phenylcarbamoylmethyl]-2,5-dioxopiperazin-1-yl]benzyloxy]-2-methylquinoline was obtained from 8-[2,6-dichloro-3-(4-carboxymethyl-2,5-dioxopiperazin-1-yl)benzyloxy]-2-methylquinoline and <strong>[6274-22-2]4-amino-N-methylbenzamide</strong> according to a similar manner to that of Example 7. NMR (CDCl3 -CD3 OD, delta): 2.62 (3H, s), 3.89 (3H, s), 4.07 (1H, d, J=16Hz), 4.18 (1H, d, J=16Hz), 4.27-4.41 (4H, m), 5.50 (2H, s), 7.19-7.30 (4H, m), 7.37-7.44 (3H, m), 7.56 (2H, d, J=8Hz), 7.70 (2H, d, J=8Hz), 8.02 (1H, d, J=8Hz).
  • 18
  • [ 346-55-4 ]
  • [ 6274-22-2 ]
  • [ 64100-39-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; EXAMPLE 6 p-[(7-trifluoromethyl-4-quinolyl)amino]-N-methylbenzamide hydrochloride A mixture of 0.1 mole of <strong>[6274-22-2]N-methyl-p-aminobenzamide</strong>, 0.1 mole of 4-chloro-7-trifluoromethylquinoline, 10 ml. of concentrated hydrochloric acid and 500 ml. of absolute ethanol is stirred at about 25 C. for 30 minutes. A precipitate begins to form, and the mixture is then heated at reflux for 4 hours. The mixture is cooled and filtered to obtain p-[(7-trifluoromethyl-4-quinolyl)amino]-N-methylbenzamide hydrochloride.
  • 19
  • [ 7285-11-2 ]
  • [ 112605-39-7 ]
  • [ 6274-22-2 ]
  • [ 841-95-2 ]
  • [ 74617-70-2 ]
YieldReaction ConditionsOperation in experiment
TSOH; In methanol; sodium tetrahydroborate; water; N,N-dimethyl-formamide; toluene; EXAMPLE XII 1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-2-(4-N-methylcarbamyl)anilino-2H-benzo[a]quinolizine (TR-3991) A mixture of 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-oxo-2H-benzo[a]quinolizine (8.7 g, 0.033 mole), 4-amino-N -methylbenzamide (6.5 g), a catalytic amount of TsOH, 250 ml of toluene and 30 ml of DMF was refluxed for 4 days with the water produced being collected in a Dean-Stark trap. The solvent was removed in vacuo whereupon the concentrate was dissolved in 150 ml of methanol, and cooled in an ice bath while 8 g of NaBH4 was added in portions. The mixture was stirred in the cold for 1 hour and refluxed for 1 hour. At this point the solvent was removed in vacuo and the concentrate dissolved in water, extracted with chloroform, dried over MgSO4 and concentrated. The concentrate was chromatographed over alumina using chloroform-acetone (9:1) as eluant to yield 9 g of product. The product was rechromatographed on silica gel using chloroform-methanol (9:1) as eluant. The 5.5 g of product was crystallized from 2-propanol/petroleum ether to yield 2.9 g of the desired product, m.p. 177-9. Anal. Calcd for C23 H29 N3 O3: C, 69.85; H, 7.39; N, 10.62; Found: C, 69.12; H, 7.36; N, 10.59.
  • 20
  • [ 934524-15-9 ]
  • [ 6274-22-2 ]
  • N-methyl-4-({7-[(4-methylphenyl)sulfonyl]-4-[(2,2,2-trifluoroethyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl}amino)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tris-(dibenzylideneacetone)dipalladium(0); XPhos; In tert-butyl alcohol; at 80℃;Product distribution / selectivity; Intermediate 12; W-Methyl-4-({7-[(4-methylphenyl)sulfonyl]-4-[(2,2,2-trifluoroethyl)amino]-7H-py rrolo[2,3-d]pyrimidin-2-yl}amino)benzamide; A mixture of 2-chloro-7-[(4-methylphenyl)sulfonyl]-lambda/-(2,2,2-trifluoroethyl)-7/-/-pyrrolo[2,3-c/]pyrimi din-4-amine (404mg), 4-amino-lambda/-methylbenzamide (180mg), tris(dibenzylideneacetone)dipalladium (0) (91.6mg),2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (47.3mg) and potassium carbonate (193mg) in t-butanol (18ml) was degassed and then heated at 8O0C under nitrogen overnight. The cooled reaction was diluted with ethyl acetate, applied to a SCX-2 SPE (5Og), the column washed with ethyl acetate and methanol and the product eluted with methanol / 0.880 ammonia. The solvents were evaporated to give the title compound as a beige foam (385mg). LC/MS; Rt 3.52min, MH+ 519.
  • 21
  • N-(1,1-dimethylethyl)-2-iodo-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
  • [ 6274-22-2 ]
  • C25H28N6O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;bis(dibenzylideneacetone)-palladium(0); DavePhos; In N,N-dimethyl-formamide; at 80℃; for 2h; Example 27; 4-({4-[(1 ,1 -Dimethylethyl)amino]-1 W-pyrrolo[2,3-d]pyrimidin-2-yl}amino)-lambda/-met hylbenzamide trifluoroacetate; lambda/-(1 J-dimethylethyl)-2-iodo-7-[(4-methylphenyl)sulfonyl]-7/-/-pyrrolo[2,3-c(]pyrimidin- 4-amine (O.betammol) was dissolved in DMF (16ml). Bis(dibenzylideneacetone) palladium (10mol%, Aldrich), 2-dicyclohexylphosphino-2'-(lambda/,lambda/-dimethylamino) biphenyl (15mol%), cesium carbonate (0.3mmol) and 4-amino-lambda/-methylbenzamide (0.15mmol) were combined with an aliquot of this solution (2ml). The reaction was heated at 800C for 2h, allowed to cool, filtered through Celite and concentrated. The reaction was dissolved in methanol (1.5ml), treated with sodium methoxide in methanol (0.5M, 500mul), stirred at 700C for 2h and left to stand at room temperature overnight. The reaction was heated for a further 5h, concentrated and purified using MDAP. The fractions containing product were evaporated to dryness to give title compound (3mg). LC/MS; Rt 2.58min, MH+ 339.
  • 22
  • 2-iodo-7-[(4-methylphenyl)sulfonyl]-N-(2,2,2-trifluoroethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
  • [ 6274-22-2 ]
  • N-methyl-4-({7-[(4-methylphenyl)sulfonyl]-4-[(2,2,2-trifluoroethyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl}amino)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;bis(dibenzylideneacetone)-palladium(0); DavePhos; In N,N-dimethyl-formamide; at 80℃; for 3h;Product distribution / selectivity; Method 5:; 2-lodo-7-[(4-methylphenyl)sulfonyl]-lambda/-(2,2,2-trifluoroethyl)-7H-pyrrolo[2,3-c/]pyrimidi n-4-amine (992mg) was suspended in DMF (20ml). An aliquot (1ml) of this mixture was treated with a solution of the aniline (0.2mmol) in DMF (1ml), cesium carbonate (97.5mg), 2-dicyclohexylphosphino-2'-(lambda/,lambda/-dimethylamino)biphenyl (5.8mg) and bis(dibenzylideneacetone) palladium (5.8mg). The reaction was stirred at 80C EPO <DP n="52"/>under nitrogen for 3h. The reaction was filtered through Celite, concentrated (vacuum centrifuge) and the residue dissolved in methanol (1ml), treated with sodium methoxide in methanol (0.5M, 500mul) and stirred at 6O0C overnight. The reaction was concentrated and purified using MDAP. The appropriate fractions were reduced to dryness to give the title compound.
  • 23
  • 2-iodo-7-[(4-methylphenyl)sulfonyl]-N-[(1R)-1-methylpropyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
  • [ 6274-22-2 ]
  • C25H28N6O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;bis(dibenzylideneacetone)-palladium(0); DavePhos; In N,N-dimethyl-formamide; at 80℃; for 3h; Method 2:; Pyrrolo[2,3-cdpyrimidin-4-amine reagent, for example,Pyrrolo[2,3-c/]pyrimidin-4-amine (O.i mmol, 43mg), 4-amino-lambda/-methylbenzamide (29.8mg, Asinex), cesium carbonate (96mg), bis(dibenzylideneacetone)palladium (6mg, Acros) and 2-dicyclohexylphosphino-2'-(lambda/,lambda/-dimethylamino)biphenyl (6mg, Acros) were combined in DMF (2.0ml). The reaction mixture was heated at 800C for 3h. The reaction mixture was allowed to cool, filtered through Celite, the Celite washed with DMF and the combined filtrate and washings evaporated to dryness. The residue was heated with sodium methoxide solution (2N, 0.5ml) at 800C for 2h and allowed to cool to room temperature. The solution was evaporated to dryness, the residue dissolved in DMSO and purified by MDAP. The fractions containing product were evaporated to dryness to give the desired compound.
  • 24
  • [ 19099-93-5 ]
  • [ 6274-22-2 ]
  • [ 1037834-46-0 ]
YieldReaction ConditionsOperation in experiment
86% Alternatively the compound of Example 20 can be made by the following three steps followed by steps 6-9 as described above. 1) 4-(4-methylaminocarbonyl-phenylamino)-piperidine-1-carboxylic acid benzyl ester hydrogen chloride; 4-arnino-N-methylbenzamide (7.51 g, 50.0 mmol), benzyl 4-oxo-1-piperidinecarboxylate (14.0 g, 60.0 mmol) and acetic acid (2.86 mL, 50.0 mmol) were added to dichloroethane (90 mL). Sodium triacetoxyborohydride (15.9 g, 75 mmol) was added in three portions over a period of 6 hours. The mixture was stirred at room temperature for 18 hours and then slowly added to water (20 mL). 3M aq. sodium hydroxide (50 mL) was added to adjust pH to 13. The organic layer was isolated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with sat. aq. sodium bicarbonate and brine, and dried over magnesium sulfate. The filtrates were concentrated to dryness. Methanol (90 mL) was added. The solution was heated to 7O0C. 4.5M hydrogen chloride in isopropanol (12 mL, 54 mmol) was added. The slurry was stirred at 7O0C for 2 hours, 220C for 1 hour, and then filtered. The cake was washed with Methyl t-butyl ether and dried under vacuum to give 4-(4-methylaminocarbonyl- <n="68"/>phenylamino^piperidine-i-carboxylic acid benzyl ester hydrogen chloride (17.4 g) as a white powder in 86% yield. LC-MS APCI (m/z) 368 (M+H)+; 1H NMR (400 MHz, DMSO- dbeta): delta 8.21 (brs, 1 H), 7.69 (d, 2 H), 7.32 (m, 5 H), 6.92 (brs, 2 H), 5.03 (s, 2 H), 3.96 (d, 2 H), 3.53 (m, 1 H), 2.91 (brs, 2 H), 2.70 (s, 3 H), 1.86 (d, 2 H), 1.36 (m, 2 H).
  • 25
  • [ 108-77-0 ]
  • [ 6274-22-2 ]
  • [ 7336-20-1 ]
  • [ 74-89-5 ]
  • C38H36N14O8S2(2-)*2Na(1+) [ No CAS ]
  • 26
  • [ 108-77-0 ]
  • [ 6274-22-2 ]
  • [ 7336-20-1 ]
  • C36H28Cl2N12O8S2(2-)*2Na(1+) [ No CAS ]
  • 27
  • [ 6274-22-2 ]
  • [ 3932-97-6 ]
  • [ 1073160-19-6 ]
YieldReaction ConditionsOperation in experiment
40% Preparation of 4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-N-methylbenzamide (B20) ; A solution of 2,4-dichloro-5-trifluoromethyl-pyrimidine (8.63 mmol) in 1:1 t-BuOH/DCE (10 mL) was cooled to 5 C., treated with solid ZnBr2 (22.5 mmol), and stirred at 5 C. for 30 minutes. The resultant solution was maintained at 5 C. and treated first with solid <strong>[6274-22-2]4-amino-N-methyl-benzamide</strong> (7.5 mmol) followed by TEA (16.5 mmol). The resultant white mixture was allowed to warm 25 C., and it was mixed at 25 C. for 20 hours. The mixture was adsorbed onto silica gel, and the fraction eluting 0-10% methanol/DCM was collected and concentrated. The resultant residue was triturated with water and filtered to provide B20. Yield: 3.0 mmol, 40%. LCMS 2.3 min, MZ+=331.1 1H NMR (500 MHz, d6-DMSO) delta ppm 10.89 (s, 1H), 8.87 (s, 1H), 8.34 (d, J=4.67 Hz, 1H), 7.73-7.89 (m, 3H), 2.78 (d, J=4.67 Hz, 3H).
  • 28
  • [ 1187890-13-6 ]
  • [ 6274-22-2 ]
  • [ 1187889-73-1 ]
YieldReaction ConditionsOperation in experiment
40% With diisopropyl-carbodiimide; In tetrahydrofuran; Example 23 Synthesis of N-Methyl-4-{3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionylamino}-benzamide 4-Amino-N-methyl-benzamide (40 g, 0.3 mol) was added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (100 mg, 0.3 mmol) and DIC (50 mg, 0.4 mmol) in THF (2 mL) and the mixture was stirred overnight. The resulting precipitate was filtered and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using basic alumina (methanol in chloroform) to afford 56 mg (40%) of N-methyl-4-{3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionylamino}-benzamide. LCMS: 477.17 (M+1)+, 94.5%, 1H NMR: (DMSO-d6): delta 7.8 (m, 2H), 7.6 (m, 4H), 7.4 (m, 1H), 4.0 (m, 2H), 3.8 (m, 4H), 3.6 (m, 3H), 3.2 (m, 2H), 3.0 (d, 3H).
  • 29
  • [ 1027133-60-3 ]
  • [ 6274-22-2 ]
  • [ 1027133-61-4 ]
YieldReaction ConditionsOperation in experiment
19% Example 5 Method H: 4-(4-(5,6,7,8-tetrahydro-7,7-dimethyl-4-oxo-4H-thiazolo[5,4-c]azepin-2-yl)pyridin-2-ylamino)-N-methylbenzamide (I-5) 2-(2-chloropyridin-4-yl)-5,6,7,8-tetrahydro-7,7-dimethylthiazolo[5,4-c]azepin-4-one (70 mg, 1.0 Eq.), <strong>[6274-22-2]4-amino-N-methyl-benzamide</strong> (41 mg, 1.2 Eq.), NaOtBu (61 mg, 2.8 Eq.), Pd(OAc)2 (5 mg, 0.1 Eq.) were suspended/dissolved in dry toluene and degassed (vacuum/N2 cycles*5). 2-Di-tert-butylphosphino)biphenyl (143 mg, 0.2 Eq.) was then added. The resultant mixture was then refluxed overnight. A further portion of NaOtBu (61 mg, 2.8 Eq.), Pd(OAc)2 (5 mg, 0.1 Eq.) and 2-(di-tert-butylphosphino)biphenyl (14 mg, 0.2 Eq.) were added, followed by dry dioxane (0.5 mL). The resultant mixture was refluxed for a further night. The reaction mixture was allowed to cool to RT, partitioned between EtOAc/MeOH (3:1)/NH4Cl, and then extracted into EtOAc/MeOH (3:1) (3*50 mL). The combined organic layers were washed with brine (1*20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification was achieved using column chromatography (10% MeOH/90% DCM) to obtain the title compound as a bright yellow powder (18.6 mg, 19% yield); 1H NMR (DMSO D6) 1.0 (6H, s), 2.8 (3H, d), 3.0 (2H, s), 3.0 (2H, m), 7.3 (1H, m), 7.5 (1H, s), 7.8 (4H, s), 8.2 (1H, m), 8.3 (2H, m), 9.6 (1H, s); LC/MS M+1 (obs.) 422.20; LC/MS M-1 (obs.) 420.30.
  • 30
  • [ 108-77-0 ]
  • [ 6274-22-2 ]
  • [ 81-11-8 ]
  • C36H28Cl2N12O8S2(2-)*2Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
400 G of ice-water and 120 G (0.65 mol) of cyanuric chloride dissolved in 753 g of methyl ethyl ketone are introduced into a 2.5 litre flat-flanged flask equipped with a condenser, stirrer and pH meter. Then, in the course of 65 min, 977 ML of a 12 % solution of 4,4'- diaminostilbene-2, 2'-disulfonic acid in soda water are slowly added dropwise at pH 4.5-5. 0 so that no excess of disulfonic acid is formed. When the addition is complete, stirring is carried out at an intemal temperature OF 5-10C for a further 10 min. Then, in the course of 15 min, 97.6 G (0.65 mol) OF 4-AMINO-N-METHYLBENZAMIDE ARE intro- duced at 10-20C and pH 7.0-7. 5 into the resulting yellow suspension. The yellow suspension is then heated to 72C in the course of one hour and stirred at that temperature for a further 2 h. After the solvent has been distilled off, a further 200 mi of water are added and the mixture is stirred for a further 1.5 h at 85C. After cooling to 75C, the crude product is filtered through a suction filter, washed with 2.5 % NACI solution and dried in vacuo at 80C. Yield : 306.1 G Appearance: yellow crystals
  • 31
  • [ 6274-22-2 ]
  • [ 40131-09-7 ]
  • [ 1256468-44-6 ]
YieldReaction ConditionsOperation in experiment
94% In toluene; at 100℃; for 3h; (c) Preparation of intermediary compound 2-[(4-Methylcarbamoyl-phenylamino)- methylenejmalonic acid diethyl ester:To a solution of 4-amino-iV-methyl-benzamide (7.5 g, 50 mmol) in anhydrous toluene (15 mL) was added diethoxymethylene malonate (11.88 g, 55.0 mmol) at room temperature. The reaction mixture was stirred at 100 0C for 3 hours, cooled to 40 0C and petroleum ether (200 mL) was added and the reaction mixture was subsequently stirred for 30 minutes. The solid formed, was collected by filtration, washed with diisopropylether and dried in vacuo to afford 15.0 g (94 % yield) of 2-[(4-methylcarbamoylphenylamino)methylene]malonic acid diethyl ester as a white solid. 1H-NMR (300 MHz, CDCl3) delta 11.09 (d, J= 13.5 Hz, IH), 8.54 (d, J= 13.5 Hz, 2H), 7.81 (d, J= 8.4 Hz, 2H), 7.18 (d, J= 8.7 Hz, 2H), 6.20 (bs, IH), 4.36-4.24 (m, 4H), 3.03 (d, J= 4.8 Hz, 3H), 1.41-1.33 (m, 6H). LC-MS (m/z, 0A): 319.6 (M-I, 99.7).
  • 32
  • [ 96-31-1 ]
  • [ 150-13-0 ]
  • [ 6274-22-2 ]
  • 33
  • [ 6274-22-2 ]
  • [ 41466-49-3 ]
  • 34
  • [ 6274-22-2 ]
  • C12H13N3O2 [ No CAS ]
  • 35
  • [ 6274-22-2 ]
  • [ 1270120-36-9 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 6274-22-2 ]

Aryls

Chemical Structure| 6331-71-1

A101804 [6331-71-1]

4-Amino-N,N-dimethylbenzamide

Similarity: 0.93

Chemical Structure| 4141-08-6

A139144 [4141-08-6]

2-Amino-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 774-67-4

A147441 [774-67-4]

4-Amino-N-isopropylbenzamide

Similarity: 0.93

Chemical Structure| 953739-92-9

A103019 [953739-92-9]

4-Amino-N,N,3-trimethylbenzamide

Similarity: 0.91

Chemical Structure| 2835-68-9

A401089 [2835-68-9]

4-Aminobenzamide

Similarity: 0.88

Amides

Chemical Structure| 6331-71-1

A101804 [6331-71-1]

4-Amino-N,N-dimethylbenzamide

Similarity: 0.93

Chemical Structure| 4141-08-6

A139144 [4141-08-6]

2-Amino-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 774-67-4

A147441 [774-67-4]

4-Amino-N-isopropylbenzamide

Similarity: 0.93

Chemical Structure| 953739-92-9

A103019 [953739-92-9]

4-Amino-N,N,3-trimethylbenzamide

Similarity: 0.91

Chemical Structure| 675109-45-2

A197166 [675109-45-2]

6-Amino-2,3-dihydro-1H-isoindol-1-one

Similarity: 0.91

Amines

Chemical Structure| 6331-71-1

A101804 [6331-71-1]

4-Amino-N,N-dimethylbenzamide

Similarity: 0.93

Chemical Structure| 4141-08-6

A139144 [4141-08-6]

2-Amino-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 774-67-4

A147441 [774-67-4]

4-Amino-N-isopropylbenzamide

Similarity: 0.93

Chemical Structure| 953739-92-9

A103019 [953739-92-9]

4-Amino-N,N,3-trimethylbenzamide

Similarity: 0.91

Chemical Structure| 675109-45-2

A197166 [675109-45-2]

6-Amino-2,3-dihydro-1H-isoindol-1-one

Similarity: 0.91