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Chemical Structure| 49851-36-7 Chemical Structure| 49851-36-7

Structure of 49851-36-7

Chemical Structure| 49851-36-7

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Product Details of [ 49851-36-7 ]

CAS No. :49851-36-7
Formula : C9H12ClNO2
M.W : 201.65
SMILES Code : O=C(OC)CC1=CC=CC=C1N.[H]Cl
MDL No. :MFCD07371496

Safety of [ 49851-36-7 ]

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

Application In Synthesis of [ 49851-36-7 ]

* 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 [ 49851-36-7 ]

[ 49851-36-7 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 49851-36-7 ]
  • [ 143782-18-7 ]
  • C18H14F3N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 20℃; 5.3 ml of a 20% solution of phosgene in toluene were initially charged under an argon atmosphere and admixed dropwise at 75 C. with a solution of 1 g of 4-amino-2-trifluoromethylbenzonitrile in 25 ml of dry acetonitrile; then the mixture was stirred at 75 C. for 2 h. The reaction mixture was concentrated under reduced pressure, taken up in toluene and concentrated again. The residue was dissolved in 20 ml of tetrahydrofuran and admixed with 1 g of <strong>[49851-36-7]methyl 2-aminophenylacetate hydrochloride</strong>. To this mixture were slowly added dropwise 1.05 ml of triethylamine with stirring and the reaction mixture was then stirred at room temperature for 8 h. Finally, 5 ml of concentrated hydrochloric acid were added and the mixture was heated under reflux for 8 h. Thereafter, the cooled reaction mixture was admixed cautiously with saturated sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate; the organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography (method [RP1]). This afforded 120.1; molecular weight 345.07 (C17H10F3N3O2); retention time Rt=2.04 min. [B]; MS(ES-): 344.51 (M-H+).
  • 2
  • [ 1038695-04-3 ]
  • [ 49851-36-7 ]
  • [ 1038695-07-6 ]
  • 3
  • [ 4684-94-0 ]
  • [ 49851-36-7 ]
  • methyl 2-(2-(6-chloropicolinamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2.5h;Inert atmosphere; ln a 40 mL vial, HATU (2.263 g, 5.95 mmol) was added in one portion at room temperature to a DMF solution (10 mL) of <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 49851-36-7) (1g, 4.96 mmol), 6-chloropyridine-2-carboxylic acid (CAS 4684-94-0) (0.938 g, 5.95 mmol) and DIEA (2.165 mL, 12.40 mmol). The resulting solution was allowed to stir at room temperature (2.5 hr). The reaction was diluted with ethyl acetate, washed with water (twice) and a saturated aq. NaCI solution. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified via FCC (10:1 Heptane/ethyl acetate to 1 :1 Heptane/ethyl acetate) to give the title compound. MS (ESI+) m/z 305.3 (M+H).
  • 4
  • [ 269409-73-6 ]
  • [ 49851-36-7 ]
  • methyl 2-(2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
TEA (1.685 mL, 12.09 mmol) was added to a mixture of 3-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)benzoic acid (CAS 269409-73-6) (1 g, 4.03 mmol) and HATU (1.686 g, 4.43 mmol) in DMF (4.5 mL). After 30 min, <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 49851-36-7) (0.666 g, 4.03 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction was diluted with a 4:1 EtOAc/heptanes mixture and water. The aqueous phase was extracted with 4:1 EtOAc/heptanes. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (heptane/EtOAc with 10% MeOH, 100:0 to 0:100) to give the title compound. MS (ESI+) m/z 396.4 (M+H).
  • 5
  • [ 49851-36-7 ]
  • 3'-(((tert-butoxycarbonyl)amino)methyl)-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
  • methyl 2-(2-(3'-(((tert-butoxycarbonyl)amino)methyl)-[1,1'-biphenyl]-3-ylcarboxamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
TEA (0.255 ml_, 1.833 mmol) was added to a mixture of 3'-{{{tert- butoxycarbonyl)amino)methyl)-[1 ,1 '-biphenyl]-3-carboxylic acid (200 mg, 0.61 1 mmol) and HATU (256 mg, 0.672 mmol) in DMF at 23 C. After 15 min, <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 35613-44-6) (130 mg, 0.61 1 mmol) was added and the resulting mixture was stirred at room temperature overnight. The resulting mixture was partitioned between with EtOAc and H20. The layers were separated and the aqueous layer was extracted with 4:1 EtOAc/heptane. The combined organics were washed with 5% aqueous LiCI solution, the washed organics were dried with Na2S04, the dried solution was filtered, and the filtered solution was concentrated. The resulting crude was purified by silica gel chromatography (10- 70% EtOAc/heptanes) to provide the title compound. MS (ESI ) m/z 473.4 (M-H).
  • 6
  • [ 585-76-2 ]
  • [ 49851-36-7 ]
  • methyl 2-(2-(3-bromobenzamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 0.5h;Inert atmosphere; TEA (0.276 ml_, 1 .984 mmol) was added to a mixture of 3-bromobenzoic acid (199 mg, 0.992 mmol) and HATU (415 mg, 1 .091 mmol) in DMF at 23 C. In a separate vial, methyl 2-(2- aminophenyl)acetate hydrochloride (CAS 49851 -36-7) (200 mg, 0.992 mmol) was stirred with TEA (0.276 ml_, 1 .980 mmol) in DMF (0.5 ml_). After 5 min, the solution of methyl 2-(2- aminophenyl)acetate hydrochloride (200 mg, 0.992 mmol) was added to the 3-bromobenzoic acid (199 mg, 0.992 mmol) mixture and the resulting mixture was stirred at rt for 30 min. The reaction mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organics were washed with 5% aq LiCI, dried (Na2S04) and concentrated. The resulting residue was purified by silica gel chromatography (EtOAc- heptanes 0-60%) to provide the title compound. MS (ESI+) m/z 348.0, 350.0 (M+H).
With triethylamine; HATU; In N,N-dimethyl-formamide; at 23℃; for 0.583333h; Intermediate 36. Methyl 2-(2-(3-bromobenzamido)phenyl)acetate TEA (0.276 ml_, 1 .984 mmol) was added to a mixture of 3-bromobenzoic acid (199 mg, 0.992 mmol) and HATU (415 mg, 1 .091 mmol) in DMF at 23 C. In a separate vial, methyl 2-(2- aminophenyl)acetate hydrochloride (CAS 49851 -36-7) (200 mg, 0.992 mmol) was stirred with TEA (0.276 ml_, 1 .980 mmol) in DMF (0.5 ml_). After 5 min, the solution of methyl 2-(2- aminophenyl)acetate hydrochloride (200 mg, 0.992 mmol) was added and the resulting mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organics were washed with 5% aq LiCI, dried (Na2S04) and concentrated. The resulting residue was purified by silica gel chromatography (EtOAc- heptanes 0-60%) to provide the title compound. MS (EST) m/z 348.0, 350.0 (M+H).
  • 7
  • [ 49851-36-7 ]
  • 3-bromo-5-(methylcarbamoyl)benzoic acid [ No CAS ]
  • methyl 2-(2-(3-bromo-5-(methylcarbamoyl)benzamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of 3-bromo-5-(methylcarbamoyl)benzoic acid (210 mg, 0.814 mmol) in dichloromethane (8 mL), oxalyl chloride (0.107 mL, 1.22 mmol) and DMF (0.006 mL, 0.081 mmol) were added at 0 C. After 15 minutes, <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 35613-44-6) (269 mg, 1.63 mmol) was added and the reaction stirred for 2 h. The reaction mixture was purified using silica gel chromatography (EtO Ac- heptane 1 :1 ) to provide the title compound. MS (ESI+) m/z 405.2, 407.1 (M+H).
  • 8
  • [ 49851-36-7 ]
  • [ 88982-82-5 ]
  • methyl 2-(2-(4-bromothiazole-2-carboxamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a suspension of 4-bromothiazole-2-carboxylic acid (CAS 88982-82-5) (0.1 12 g, 0.538 mmol) in DCM (5.38 mL) and DMF (8.34 mu, 0.108 mmol) was added oxalyl chloride (0.059 mL, 0.67 mmol) and this was stirred at room temperature. After 30 minutes the reaction was concentrated. The solid was dissolved in DCM (5.38 mL), and methyl 2-(2- aminophenyl)acetate hydrochloride (CAS 35613-44-6) (0.089 g, 0.538 mmol) and DIPEA (0.188 mL, 1 .077 mmol) were added and the reaction was stirred at room temperature. After 5 minutes the reaction was partially concentrated and then purified directly by flash chromatography (0-50% EtOAc: Heptanes) to provide the title compound. MS (ESI-) m/z 353.1 , 355.1 (M-H).
  • 9
  • [ 49851-36-7 ]
  • [ 140472-69-1 ]
  • methyl 2-(2-(3-bromo-5-hydroxybenzamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
TEA (2.248 mL, 16.13 mmol) was added to a mixture of 3-bromo-5-hydroxybenzoic acid (CAS 140472-69-1 ) (1000 mg, 4.61 mmol), <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 49851-36-7) (978 mg, 4.61 mmol) and HATU (1927 mg, 5.07 mmol) in DMF (10 mL) at 23 C. The resulting mixture was stirred at rt overnight. To the mixture was added K2C03 (191 1 mg, 13.82 mmol) and the mixture was heated to 100 C for 2 hours. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was concentrated and the residue was purified by flash column on silica gel (EtOAc-heptane 0-100%) to give the title compound. MS (ESI+) m/z 364.1 , 366.1 (M+1 ).
  • 10
  • [ 49851-36-7 ]
  • [ 78238-11-6 ]
  • methyl 2-(2-(3-acetamido-5-bromobenzamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; HATU; In N,N-dimethyl-formamide; at 20 - 23℃;Inert atmosphere; TEA (0.324 mL, 2.325 mmol) was added to a mixture of 3-acetamido-5-bromobenzoic acid (CAS 78238-1 1 -6) (200 mg, 0.775 mmol) and HATU (324 mg, 0.852 mmol) in DMF (3 mL) at 23 C. After 5 min, <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 49851 -36-7) (165 mg, 0.775 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was partitioned between 4: 1 EtOAc/heptanes and water. The aqueous layer was extracted with 4: 1 EtOAc/heptanes. The combined organic layers were washed with 5% aqueous LiCI solution, the organics were dried (Na2S04), filtered and concentrated. The residue was purified by silica gel chromatography (EtOAc/heptanes 20-80%) to provide the title compound. MS (ESI+) m/z 405.2, 407.2 (M+H).
  • 11
  • [ 49851-36-7 ]
  • 3-bromo-5-propionamidobenzoic aicd [ No CAS ]
  • methyl 2-(2-(3-bromo-5-propionamidobenzamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 48h; TEA (0.231 mL, 1 .654 mmol) was added to a mixture of 3-bromo-5- propionamidobenzoic acid (0.15 g, 0.551 mmol) and HATU (0.231 g, 0.606 mmol) in DMF (2 mL). After 10 min, <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 49851 -36-7) (0.1 1 1 g, 0.551 mmol) was added and the resulting mixture was stirred at room temperature for 48h. The reaction was diluted with EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2S04, filtered and evaporated. The crude material was purified by flash column chromatography on silica gel (heptane/EtOAc = 100:0 to 0: 100) to give the title compound. 1H NMR (400 MHz, DICHLOROMETHANE-c 2) delta ppm 9.49 (br. s., 1 H), 8.16 (s, 1 H), 7.90 - 7.95 (m, 2 H), 7.83 (t, J=1 .5 Hz, 1 H), 7.33 - 7.39 (m, 2 H), 7.29 (dd, J=7.6, 1 .3 Hz, 1 H), 7.18 (td, J=7.6, 1 .3 Hz, 1 H), 3.77 (s, 3 H), 3.72 (s, 2 H), 2.41 (q, J=7.6 Hz, 2 H), 1 .22 (t, J=7.6 Hz, 3 H).
  • 12
  • [ 49851-36-7 ]
  • methyl 2-(2-amino-5-bromophenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 0.166667h;Inert atmosphere; To a solution of <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 49851-36-7) (0.50 g, 2.5 mmol) in DMF (24.8 ml) at 0 C was added NBS (0.441 g, 2.48 mmol) and this was stirred at 0 C. After 10 minutes the reaction was quenched with saturated aqueous sodium bicarbonate, extracted with EtOAc, washed with water, dried over MgS04, filtered and concentrated. This was purified by flash chromatography (0-15% EtOAc:DCM) to provide the title compound. MS (ESI+) m/z 244.1 , 246.1 (M+H).
  • 13
  • [ 4684-94-0 ]
  • [ 49851-36-7 ]
  • 2-(2-(6-(3-(aminomethyl)phenyl)picolinamido)phenyl)acetic acid [ No CAS ]
  • 14
  • [ 49851-36-7 ]
  • 3'-(((tert-butoxycarbonyl)amino)methyl)-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
  • methyl 2-(2-( 3'-(aminomethyl)-[1,1'-biphenyl]-3-ylcarboxamido)phenyl)acetate trifluoroacetate [ No CAS ]
  • 15
  • [ 585-76-2 ]
  • [ 49851-36-7 ]
  • 2-(2-(3'-(aminomethyl)-[1,1'-biphenyl]-3-ylcarboxamido)phenyl)acetic acid [ No CAS ]
 

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