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Product Details of [ 94838-59-2 ]

CAS No. :94838-59-2 MDL No. :MFCD05663961
Formula : C13H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HOPALBZGTWDOTL-UHFFFAOYSA-N
M.W : 236.31 Pubchem ID :382207
Synonyms :

Calculated chemistry of [ 94838-59-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 6
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 69.17
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 2.07
Log Po/w (SILICOS-IT) : 1.73
Consensus Log Po/w : 2.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.656 mg/ml ; 0.00278 mol/l
Class : Soluble
Log S (Ali) : -3.19
Solubility : 0.154 mg/ml ; 0.000652 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.81
Solubility : 0.0369 mg/ml ; 0.000156 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 94838-59-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 94838-59-2 ]

* 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.

  • Upstream synthesis route of [ 94838-59-2 ]
  • Downstream synthetic route of [ 94838-59-2 ]

[ 94838-59-2 ] Synthesis Path-Upstream   1~11

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YieldReaction ConditionsOperation in experiment
81% With ammonium formate In ethanol; water at 80℃; for 1 h; To a solution of [2-(4-nitro-phenyl)-ethyl]-carbamicacid te/t-butyl ester (18.7 g, 70.30 mmol) in ethanol (200 ml) a slurry of 10percent palladium on charcoal (2 g) in water (10 ml) was added. At 800C ammonium formate (44.3 g, 703 mmol) in wa.not. ter (90 ml) was added slowly. After complete addition the mixture was stirred at 800C for 1 h. The mixture was allowed to come to room temperature, filtered and concentrated in vacuo. The residue was diluted with water and extracted twice with dichloromethane. The combined organic layers were washed with water, dried over MgSO4, filtered and the solvent evaporated under reduced pressure to give the product as a yellow oil (13.5 g, 81percent).
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5627 - 5631
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 10, p. 2852 - 2855
[3] Patent: WO2008/13997, 2008, A2, . Location in patent: Sheet 9
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2845 - 2854
[5] Patent: WO2006/40179, 2006, A1, . Location in patent: Page/Page column 99
[6] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4264 - 4269
[7] Bioorganic and medicinal chemistry letters, 2003, vol. 13, # 2, p. 209 - 212
[8] Patent: WO2005/30678, 2005, A2, . Location in patent: Page/Page column 40
[9] Patent: US2003/225106, 2003, A1, . Location in patent: Page 49; 113
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YieldReaction ConditionsOperation in experiment
98% at 0 - 20℃; for 1 h; STEP 2. tert-butyl 2-(4-aminophenyl)ethylcarbamate
To a stirred solution of 2-(4-aminophenyl)ethylamine (10.0 g, 73.4 mmol) in tetrahydrofuran (150 mL) was added di-t-butyl dicarbonate (16.0 g 73.4 mmol) in tetrahydrofuran (100 mL) at 0° C.
Then, the mixture was stirred at ambient temperature for 1 h.
The volatile components were removed by evaporation and the residue was dissolved in ethyl acetate.
The organic phase was washed with water and dried (MgSO4).
Concentration of the organic solvent gave the 17.0 g (98percent) of the title compound as a colorless powder. MS (ESI) m/z 237 [M+H]+, 1H-NMR (CDCl3) δ1.43 (9H, s), 2.68 (2H, t, J=7.0 Hz), 3.26-3.38 (2H, m), 3.60 (2H, br), 4.53 (1H, br), 6.64 (2H, d, J=8.4 Hz), 6.97 (2H, d, J=8.3 Hz).
92% With triethylamine In dichloromethane at 20℃; General Procedures for the syntheses of aminesGeneral procedure AP: Boc protection of long and short chain amino anilinesTo a stirred solution of amine (1.0 eq), TEA (2 eq) in DCM (25 vol) was added di-tert-butyl dicarbonate, (1.1 eq). The mixture was stirred overnight at ambient temperature. The mixture was concentrated in vacuo and purified by FCC eluting with EtOAc :Heptane, 1 :3.; tert-Xi\\ty\\ [2-(4-aminophenyl)ethyl] carbamate I ntlThe title compound was prepared according to general procedure AP using 2-(A- aminophenyl)ethylamine (1.0 g, 7.3 mmol), TEA (2 mL, 14 mmol), DCM (25 mL), and di- tert-butyl dicarbonate (1.7 g, 7.7 mmol). The title product was obtained as a white solid. No further purification was required. Yield: 1.6 g, 92 percent.
83% at 25℃; A solution of 2-aminoethylaniline (5.0 g) and Boc2O (6.8 g) in CH2Cl2 (200 mL) was stirred at 25° C. overnight. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1:1 as eluant) to give Intermediate 252-I (6.8 g) in a 83percent yield. 222-III (7.3 g) prepared from Example 222 was added to a solution of Intermediate 252-I (6.8 g) in CH2Cl2 (250 mL). The mixture was stirred at 25° C. for 1.5 hour. NaBH(OAc)3 (6.0 g) and a small amount of MeOH were added at 0° C. The mixture was stirred at room temperature overnight. After the solution was concentrated, a saturated solution of NaHCO3 (250 mL) was added. The mixture was extracted with EtOAc, dried over anhydrous MgSO4, filtered, and cocnetrated to afford crude Intermediate 252-II (6.0 g). Crude Intermediate 252-II (3.0 g) in MeOH (15 mL) was hydrogenated in the presence of 5percent Rh/C (300 mg) and 10percent Pd/C (300 mg) at 50 psi at room temperature for 72 hours. The mixture was then filtered and concentrated. The resultant residue was purified by column chromatography on silica gel (EtOAc/MeOH=1:1) to afford Intermediate 252-III (2.6 g) in a 87percent yield. A solution of intermediate 252-III (1.5 g) treated with 1M HCl in ether (52 mL) and MeOH (10 mL) was stirred at room temperature for 8 hours. After dditional ether was added, the solution was filtered. The solid thus obtained was dried under vacuum. K2CO3 was added to a suspension of the solid in CH3CN at room temperature for 10 minutes. After water was added, the reaction mixture was stirred at room temperature for 2 hours, filtered, dried over anhydrous MgSO4, and concentrated to afford crude Intermediate 252-IV (1.5 g). Intermediate 252-IV (1.5 g) and Et3N (0.5 mL) in 1-pentanol (14 mL) was allowed to react with 2,4-dichloro-6-aminopyrimidine (1.0 g) at 120° C. overnight. The solvent was then removed to afford crude Intermediate 252-V (2.0 g). A solution of Intermediate 252-V (2.0 g) and Boc2O (2.1 g) in CH2Cl2 (250 mL) was added to Et3N (1.0 mL) at 25° C. overnight. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1:1) to give Intermediate 252-VI (1.7 g) in a 56percent yield. N1-Morpholine-N1-piperazine ethane (300 mg) was added to Intermediate 252-VI (300 mg) in 1-pentanol (1 mL). The mixture was stirred at 120° C. overnight and then concentrated. The residue thus obtained was coated with SiO2 and purified by column chromatography on silica gel (EtOAc/MeOH=1/1) to afford Intermediate 252-VII (260 mg) in a 70percent yield. A solution of 20percent TFA/CH2Cl2 (5 mL) was added to a solution of Intermediate 252-VII (260 mg) in CH2Cl2 (2 mL). The reaction mixture was stirred for 8 hours at room temperature and concentrated by removing the solvent. The resultant residue was purified by column chromatography on silica gel (21percent NH3 (aq)/MeOH=1/19) to afford Compound 252 (175 mg) in a 91percent yield. Compound 252 was then treated with 1 M HCl (4 mL) in CH2Cl2 (2 mL) for 0.5 hours. After the solvents were removed, the residue was treated with ether and filtered to give hydrochloride salt of Compound 252. CI-MS (M++1): 572.5.
82% Cooling Example 14 - Preparation of tert-Butyl (4~aminophenethyl)carbamate. 4-(2-aminoethyl)aniline (5.00 grams, 36.7 mmol, 1.0 eq) was dissolved in 50 mL EtOAc and placed in a water bath. To the rapidly stirring solution, a mixture of boc anhydride (8.25 grams, 37.8 mmol, 1.03 eq) in 50 mL EtOAc was added dropwise. Upon addition of the anhydride, the mixture turned into a white slurry, which after 4 hours became a pale yellow clear solution. Reaction left overnight. The crude mixture was concentrated under reduced pressure to a pale yellow oil, diluted with 10 mL hot EtOAc and mixed with 50 mL hot heptane. The mixture was placed in an ice bath to facilitate precipitation. The white crystals were filtered and dried to yield 7.11 grams (82percent). 1H NMR (400 MHz, DMSO-d6) δ 6.82 (d, J= 7.8 Hz, 2H), 6.76 (s, 1H), 6.47 (d, J= 7.8 Hz, 2H), 4.82 (s, 2H), 3.02 (q, J= 6.4 Hz, 2H), 2.47 (m, 2H), 1.37 (s, 9H).
80% With triethylamine In water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran Step 1:
2-(4-Aminophenyl)ethyl carbamic acid tert-butyl ester
A solution of 2-(4-aminophenyl)ethylamine (1 g, 7.3 mmol) in DCM (20 mL) at room temperature was treated with triethylamine (0.82 g, 7.7 mmol).
After 10 min the solution was cooled to -5° C. Di-tert-butyldicarbonate (1.68 g, 7.7 mmol) was added portionwise over 10 min and stirred for 30 min before warming to room temperature. NaHCO3 (sat. 2 mL) was added followed by water (40 mL).
The organic layer was separated and aqueous re-extracted with DCM (*2).
The combined organic layers were dried (K2CO3) and evaporated.
The residue was purified by column chromatography on silica gel, eluding with EtOAc:hexane (1:4) to obtain the title compound (1.4 g, 80percent) as a yellow solid. 1H NMR (360 MHz, d6-DMSO) δ1.37 (9H, s), 2.49-2.51 (2H, m), 2.99-3.06 (2H, m), 4.83 (2H, s), 6.49 (2H, d, J=8.3 Hz), 6.77-6.80 (1H, m), 6.81 (2H, d, J=8.3 Hz) MS (CI)+237 (M+H)+.
75% at 20℃; for 0.25 h; [2-(4-Amino-phenyl)-ethyl]-carbamic acid tert-butyl ester; To a solution of 4-aminophenethylamine (0.136 g, 1 mmol) in dichloromethane (4 mL) at rt was added (tBoc)2 (0.218 g, 1 mmol) and allowed to stir for 15 min. The reaction mixture was poured into water and then extracted with dichloromethane (15 mL), the organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by silica gel column chromotography using 15percent EtOAc/Hexane to give the product as a colorless solid (0.175 g, 75percent)1H NMR (400 MHz, CDCl3): δ 6.97 (d, J=8.4 Hz, 2H), 6.63 (d, J=8.4 Hz, 2H), 4.51 (bs, 1H), 3.59 (s, 2H), 3.32-3.29 (m, 2H), 2.67 (t, J=7.04, 2H), 1.43 (s, 9H).13C NMR (100 MHz, CDCl3): δ 155.84, 144.77, 129.51, 128.76, 115.28, 79.03, 41.98, 35.26, 28.37.
48% at 0 - 20℃; for 18 h; Example 5: Alternative Preparation of (R)-N2- [4- (2-AMINOETHYL) PHENYL]-L- phenylethane-1, 2-diamine; a. Preparation of [2- (4-AMINOPHENYL) ethyl] carbamic acid TERT-BUTYL ester; To a suspension of 4-aminophenethylamine (65.1 g, 1.0 equiv) in dichloromethane (1.5 L) at 0 °C was added di-tert-butyl dicarbonate (99.2 g, 0.95 equiv) in dichloromethane (300 ML) dropwise. The solution was slowly warmed to room temperature and stirred for 18 hours. Water (200 mL) was added, solvents were evaporated under reduced pressure to a volume of approximately 1L, the aqueous and organic layers were separated, and the organic layer was washed with water (200 mL) followed by saturated aqueous sodium chloride (100 mL). The organic layer was dried over anhydrous sodium sulfate (40 g). The solids were filtered and the filtrate concentrated to give crude title intermediate (100.7 g) which was suspended in a mixture of hexanes (745 mL) and ethyl acetate (150 ML). The slurry was heated until a clear solution was obtained and then the solution was slowly cooled to room temperature. The resulting cystals were filtered, washed with 10 percent ethyl acetate/hexanes solution (100 ML) and dried under vacuum to provide the title intermediate (55.1 g, 48 percent yield).
1.74 g at 20℃; for 18 h; Di-tert-butyl-dicarbonate (1.60 g, 7.34 mmol) was added to a solution of   2-(4-aminophenyl)ethylamine (1.00 g, 7.34 mmol) in   EtOAc (20 mL) at rt. After stirring for 18 h, the reaction was washed with 10percent NaHCO3 and concentrated in vacuo to give a yellow semi-crystalline waxy   solid, 1.74 g. 1H NMR (400 MHz, DMSO-d6) δ 6.79-6.82 (m, 2H), 6.77 (br t, J=5.4 Hz, 1H), 6.46-6.49 (m, 2H), 4.83 (s, 2H), 2.99-3.05 (m, 2H), 2.47-2.51 (m, 2H), 1.37 (s, 9H). ES/MS calcd. for C13H20N2NaO2 259.1. Found m/z 259.1 (M+Na)+.

Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 9, p. 1661 - 1669
[2] Patent: US2003/220372, 2003, A1, . Location in patent: Page/Page column 37
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 24, p. 3123 - 3127
[4] Patent: WO2010/20556, 2010, A1, . Location in patent: Page/Page column 60
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 37, p. 9845 - 9848
[6] Archiv der Pharmazie, 2000, vol. 333, # 8, p. 267 - 274
[7] Patent: US2006/281712, 2006, A1, . Location in patent: Page/Page column 119-121
[8] Patent: WO2015/49546, 2015, A1, . Location in patent: Page/Page column 29
[9] Patent: US6395905, 2002, B1,
[10] Patent: US2008/167334, 2008, A1, . Location in patent: Page/Page column 16
[11] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3521 - 3534
[12] Patent: WO2005/30678, 2005, A2, . Location in patent: Page/Page column 47
[13] Journal of Medicinal Chemistry, 1999, vol. 42, # 18, p. 3486 - 3493
[14] Patent: WO2005/66139, 2005, A2, . Location in patent: Page/Page column 131
[15] Patent: US2003/64991, 2003, A1,
[16] Patent: US5451677, 1995, A,
[17] Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 11, p. 585 - 591
[18] Patent: US2011/275622, 2011, A1, . Location in patent: Paragraph 0328
[19] Chemistry - A European Journal, 2016, vol. 22, # 2, p. 639 - 645
[20] Patent: US2002/28832, 2002, A1,
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Reference: [1] Patent: US2002/40023, 2002, A1,
  • 4
  • [ 29968-78-3 ]
  • [ 94838-59-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4264 - 4269
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5627 - 5631
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2845 - 2854
  • 5
  • [ 7439-89-6 ]
  • [ 144226-16-4 ]
  • [ 94838-59-2 ]
Reference: [1] Patent: US2003/125339, 2003, A1,
[2] Patent: US6878714, 2005, B2,
  • 6
  • [ 13472-00-9 ]
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YieldReaction ConditionsOperation in experiment
52% With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide [2-(4-Amino-phenyl)-ethyl]-carbamic acid tert-butyl ester (Y-1).
To a mixture of 2-(4-Amino-phenyl)-ethylamine (300 mg, 2.2 mmol), ditertbutoxyanhydride (480 mg, 2.20 mmol), DMAP (54 mg, 0.44 mmol) DIEA (0.372 ml, 2.3 mmol) in DMF (80 mL), was stirred overnight at room temperature.
Insoluble particles were removed by filtration and the solvent was evaporated.
Purification of the residue on silica gel (1:3 hexane:EtOAc) gave 270 mg (52percent) of pure [2-(4-Amino-phenyl)-ethyl]-carbamic acid tert-butyl ester.
1H-NMR (300 MHz, CDCl3) δ: 1.36 (s, 9H), 2.81 (t, 2H), 3.40 (m, 2H), 3.64 (bs, 1H), 4.63(bs, 1H), 6.72(d, 2H), 7.03 (d, 2H).
Reference: [1] Patent: US6274620, 2001, B1,
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Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4264 - 4269
  • 8
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  • [ 94838-59-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5627 - 5631
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2845 - 2854
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Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 23, p. 2995 - 3000
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 21, p. 10931 - 10937
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1213 - 1218
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