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Chemical Structure| 1007881-98-2
Chemical Structure| 1007881-98-2
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Product Details of [ 1007881-98-2 ]

CAS No. :1007881-98-2 MDL No. :MFCD21496634
Formula : C18H23BrN2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZUVCUAVWIIYSEL-AWEZNQCLSA-N
M.W : 411.29 Pubchem ID :56605334
Synonyms :

Calculated chemistry of [ 1007881-98-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 101.82
TPSA : 75.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.39
Log Po/w (XLOGP3) : 3.08
Log Po/w (WLOGP) : 2.77
Log Po/w (MLOGP) : 1.87
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 2.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0431 mg/ml ; 0.000105 mol/l
Class : Soluble
Log S (Ali) : -4.34
Solubility : 0.0189 mg/ml ; 0.000046 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.63
Solubility : 0.00964 mg/ml ; 0.0000234 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.1

Safety of [ 1007881-98-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1007881-98-2 ]

* 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 [ 1007881-98-2 ]
  • Downstream synthetic route of [ 1007881-98-2 ]

[ 1007881-98-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 1007881-98-2 ]
  • [ 1007882-23-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1995 - 2012
[2] Patent: US2008/44379, 2008, A1,
[3] Patent: US2008/50336, 2008, A1,
[4] Patent: US2008/44379, 2008, A1,
[5] Patent: US2008/50336, 2008, A1,
[6] Patent: WO2009/102318, 2009, A1,
[7] Patent: WO2009/102318, 2009, A1,
  • 2
  • [ 15761-39-4 ]
  • [ 7644-04-4 ]
  • [ 1007881-98-2 ]
YieldReaction ConditionsOperation in experiment
62% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 5℃; for 1.5 h; Preparation of intermediate 1-11N,N-Diisopropylethylamine (80.0 g, 0.62 mol) was added dropwise, over 30 minutes, to a mixture of 2-amino-l-(4-bromo-phenyl)-ethanone (50 g, 0.2 mol),2-( 1 H-7-azabenzotriazo 1- 1 -yl)- 1 , 1 ,3 ,3 -tetramethyl uranium hexafluorophosphate methanaminium (HATU; 53 g, 0.21 mol), JV-Boc-L-Proline (43.0 g, 0.2 mol ) in DMF (600 mL). The reaction mixture was stirred at 5°C for 1 hour. Most of the volatile components were removed in vacuo, and the resulting residue was partitioned between ethyl acetate (600 mL) and water (300 mL). The organic layer was washed with saturated aqueous NaHCO3 (500 mL) and brine (500 mL), dried over MgSO4, the solids were removed via filtration and the solvents of the filtrate were removed under reduced pressure. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 3:1 to 1 :1) to obtain a pale yellow solid, 60 g (62percent) o f intermediate I- 11.1H NMR: CDCl3 400 MHzδ 7.85 (d, J = 8.4 Hz ,2H), 7.66 (d, J = 8.4 Hz ,2H), 4.67-4.80 (m, 2H), 4.33-4.41 (m, IH), 3.42-3.53 (m, 2H), 2.19- 2.31 (m, 2H), 1.90- 2.00 (m, 2H), 1.50 (s, 9H) 1.10
62% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 5℃; for 1 h; 1.3 preparation of intermediate Villa (PG= Boc X= Br ; A= ^O"^Step 1N,N-Diisopropylethylamine (80.0 g, 0.62 mol) was added dropwise, over 30 minutes, to a mixture of aminomethyl-(4-bromo-phenyl)-ketone (50 g, 0.2 mol),2-( 1 H-7-azabenzotriazol- 1 -yl)- 1 , 1 ,3 ,3-tetramethyl uranium hexafluorophosphate methanaminium (HATU; 53 g, 0.21 mol), N-Boc-L-Proline (43.0 g, 0.2 mol ) in DMF (600 mL). The reaction mixture was stirred at 5°C for 1 hour. Most of the volatile components were removed in vacuum, and the resulting residue was partitioned between ethyl acetate (600 mL) and water (300 mL). The organic layer was washed with saturated aqueous NaHC03 (500 mL) and brine (500 mL), dried over MgS04, the solids were removed via filtration and the solvents of the filtrate were removed under reduced pressure. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 3: 1 to 1 : 1) to obtain a pale yellow solid, 60 g (62percent) of intermediate XXIII.1H NMR: (CDCls 400 MHz): δ 7.85 (d, J = 8.4 Hz, 2H), 7.66 (d, J = 8.4 Hz, 2H), 4.67- 4.80 (m, 2H), 4.33-4.41 (m, 1H), 3.42-3.53 (m, 2H), 2.19- 2.31 (m, 2H), 1.90- 2.00 (m, 2H), 1.50 (s, 9H)
62% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 5℃; for 1.5 h; 1.9 Preparation of Intermediate I-11; N,N-Diisopropylethylamine (80.0 g, 0.62 mol) was added dropwise, over 30 minutes, to a mixture of 2-amino-1-(4-bromo-phenyl)-ethanone (50 g, 0.2 mol), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU; 53 g, 0.21 mol), N-Boc-L-Proline (43.0 g, 0.2 mol) in DMF (600 mL). The reaction mixture was stirred at 5° C. for 1 hour. Most of the volatile components were removed in vacuo, and the resulting residue was partitioned between ethyl acetate (600 mL) and water (300 mL). The organic layer was washed with saturated aqueous NaHCO3 (500 mL) and brine (500 mL), dried over MgSO4, the solids were removed via filtration and the solvents of the filtrate were removed under reduced pressure. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 3:1 to 1:1) to obtain a pale yellow solid, 60 g (62percent) of intermediate I-11.1H NMR: CDCl3 400 MHz δ 7.85 (d, J=8.4 Hz, 2H), 7.66 (d, J=8.4 Hz, 2H), 4.67-4.80 (m, 2H), 4.33-4.41 (m, 1H), 3.42-3.53 (m, 2H), 2.19-2.31 (m, 2H), 1.90-2.00 (m, 2H), 1.50 (s, 9H)
Reference: [1] Patent: WO2011/15657, 2011, A1, . Location in patent: Page/Page column 20
[2] Patent: WO2011/54834, 2011, A1, . Location in patent: Page/Page column 31-32
[3] Patent: US2012/136027, 2012, A1, . Location in patent: Page/Page column 9
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 2058 - 2073
  • 3
  • [ 59936-29-7 ]
  • [ 5467-72-1 ]
  • [ 1007881-98-2 ]
YieldReaction ConditionsOperation in experiment
91% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; DIPEA (46.6 g, 361.5 mmol) was added to a mixture of the ammonium salt BB1-b ( 30 g, 120.5 mmol), HATU (59.5 g, 156.6 mmol) and Boc-proline methyl ester (27.2 g, 126.5 mmol) in DCM (120 ml) at 0 °C. The resulting mixture was stirred overnight then concentrated in vacuum and the residue was portioned between EtOAc and water. The organic layer was washed with 1 M HCI, brine, dried and evaporated in vacuum which gave the title compound (45 g, 91 percent). MS (ESI): 411 [M+H]+ and MS (ESI): 413 [M+H]+.
Reference: [1] Patent: WO2013/95275, 2013, A1, . Location in patent: Page/Page column 34
  • 4
  • [ 15761-39-4 ]
  • [ 5467-72-1 ]
  • [ 1007881-98-2 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 20℃; for 0.5 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.166667 h;
Example 1
Synthesis of (S)-tert-butyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)pyrrolidine-1-carboxylate (1a)
A solution of N-Boc-L-Proline (5.16 g, 24.0 mmol) and HOBt.H2O (3.67 g, 24.0 mmol) was stirred at room temperature for 10 min and then treated with N-ethyl-N'-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC.HCl, 4.60 g, 24.0 mmol).
The resulting mixture was stirred at room temperature for 30 min and then treated with a yellow solution formed by stirring 2-amino-4'-bromoacetophenone hydrochloride (5.0 g, 20.0 mmol) and N,N-diisopropylethylamine (DIPEA, 2.58 g, 20 mmol) in dichloromethane (DCM, 150 ml) at room temperature for 10 min.
The resulting mixture was stirred at room temperature overnight and then filtered through Celite.(R). to remove the precipitate.
The filtrate was extracted with DCM and H2O.
The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated.
The residue was purified with column chromatography (ethyl acetate:hexanes=2:5) to yield pure product 1a as a yellow gel (7.39 g, 90percent).
83% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16 h; 2-Amino-4-bromoacetophenone hydrochloride salt (26.38 mmol) and N-Boc-L-proline (26.91 mmol) were dissolved inanhydrous dimethylformamide. HATU (28.49 mmol) was added, followed by DIPEA (83.89 mmol). The reaction mixture was stirred at room temperature for 16 hrs. The mixture was then concentrated under vacuum, diluted with EtOAc (250mL) and water (180 mL). The organic layer was separated, washed sequentially with water (180 mL) and brine (180mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc)to give compound 4 as a beige compound in 83 percent yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 1.32 (s, 9H), 1.80 (m,3H), 2.09 (m, 1H), 3.35 (m, 1H), 4.14 (m, 1H), 4.55 (m, 2H), 7.74 (d, J = 7.90 Hz, 2H), 7.91 (d, J = 7.90 Hz, 2H), 8.20 (brs, 1H).
76% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2 h; Ν,Ν-Diisopropyethylamine (3.2 g, 24.7 mmol) was added dropwise at room temperature to a heterogeneous mixture of 2-amino-l-(4-bromophenyl)ethanone hydrochloride (2.0 g, 7.98 mmol), (S)-l-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.72 g, 7.98 mmol), HATU (3.04 g, 7.98 mmol) and DMF (20 mL). After the addition was complete the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate and washed with water, IN hydrochloric acid, a saturated sodium bicarbonate solution, a saturated sodium chloride solution and dried over magnesium sulfate, filtered and concentrated. The crude product obtained was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; (0percent to 100percent ethyl acetate/hexane) to afford, (S)-tert-butyl 2-(2-(4-bromophenyl)- 2-oxoethylcarbamoyl)pyrrolidine-l-carboxylate as a white solid, (2.50 g, 76percent): ESI-LRMS m/e calcd for [M+] 410, found 411 [M+H+].
61%
Stage #1: With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.166667 h;
Intermediate 7: 1 ,1-dimethylethyl(2S)-2-([2-(4-bromophenyl)-2-A mixture of 1-[(1 ,1-dimethylethyl)oxy]carbonyl}-L-proline (50 g, 0.233mol), HATU (106 g, 0.279 mol) and DIEA (150 mL) in DMF (400mL) was stirred at ambient temperature for 10 min. 2-Amino-1-(4-bromophenyl)ethanone hydrochloride (Intermediate 4) (70g, 0.279 mol) in DMF (500 mL) was added and the resulting mixture was stirred overnight before diluted with EtOAc (4L). The solution was washed with 1 N HCI (500 mL χ 4) and brine, dried over Na2S04, concentrated. The crude product was recrystallized from a mixture of petroleum ether / ethyl acetate (2/1 ) to give 1 ,1-dimethylethyl(2S)-2-([2-(4-bromophenyl)-2- oxoethyl]amino}carbonyl)-1 -pyrrolidinecarboxylate (Intermediate 7) (58.4g, yield: 61 percent) as yellow solid. 1H NMR (300 MHz, DMSO) δ ppm 8.22 (s, 1 H), 7.93 (d, J = 8.4 Hz, 2H), 7.77 (d, J = 8.4 Hz, 2H), 4.46-4.51 (m, 2H), 4.15-4.21 (m, 1 H), 3.28-3.40 (m, 2H),1.78-1.90 (m, 4H), 1.29-1.41 (m, 9H). ES LC-MS m/z = 411.1 , 4113.1 (M+H)+ .
56% With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In N,N-dimethyl-formamide for 2 h; To a solution of 2-amino- 1 -(4-bromophenyl)ethanone hydrochloride salt (1.10 g, 4.39 mmol), (S)-l-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.02 g, 4.73 mmol), and diisopropylethylamine (3.10 mL, 17.4 mmol) in DMF (20 mL) was added 3-(diethoxyphosphoryloxy)-(l,2,3)-benzotriazin-4(3H)-one (DEPBT, 2.0 g, 6.68 mmol) and the solution was allowed to stir for 2 hours. The mixture was poured into H2O-ethyl acetate and the layers were separated. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were washed (H2O x 2, brine), dried (Na2SO4), and filtered. The solvent was removed in vacuo and the residue purified by flash column chromatography (1 : 1 hexanes: ethyl acetate) to provide (S)-tert-butyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)pyrrolidine-l- carboxylate (1.02 g, 56percent) as a colorless foam. 1HNMR (400 MHz, DMSO-d6) δ 8.16 - 8.21 (m, IH), 7.90 - 7.92 (m, 2H), 7.73 - 7.75 (m, 2H), 4.59 (dd, J = 5.7, 18.4 Hz, IH), 4.51 (dd, J = 5.7, 18.4 Hz, IH), 4.13 - 4.19 (m, IH), 3.24 - 3.27 (m, 2H, partially obscured by H2O), 2.05 - 2.12 (m, IH), 1.74 - 1.81 (m, 3H), 1.39 (s, 3H), 1.33 (3, 6H); LCMS: Anal. Calcd. for Ci8H23BrN2O4: 410; found: 411 (M+H)+.

Reference: [1] Patent: US2011/136799, 2011, A1, . Location in patent: Page/Page column 42
[2] Patent: EP2513113, 2018, B1, . Location in patent: Paragraph 0240; 0241; 0242
[3] Patent: WO2013/53657, 2013, A1, . Location in patent: Page/Page column 41
[4] Patent: WO2011/28596, 2011, A1, . Location in patent: Page/Page column 11-12
[5] Patent: WO2008/144380, 2008, A1, . Location in patent: Page/Page column 41
[6] Patent: US2009/233925, 2009, A1, . Location in patent: Page/Page column 62
[7] Patent: WO2012/18325, 2012, A1, . Location in patent: Page/Page column 149
[8] Patent: WO2013/25975, 2013, A1, . Location in patent: Page/Page column 82
[9] Patent: US2008/44379, 2008, A1, . Location in patent: Page/Page column 64-65
[10] Patent: US2008/44380, 2008, A1, . Location in patent: Page/Page column 67-68
[11] Patent: US2008/50336, 2008, A1, . Location in patent: Page/Page column 62-63
[12] Patent: WO2008/144380, 2008, A1, . Location in patent: Page/Page column 39
[13] Patent: WO2009/102318, 2009, A1, . Location in patent: Page/Page column 108
[14] Patent: WO2010/117635, 2010, A1, . Location in patent: Page/Page column 76-77
  • 5
  • [ 99-73-0 ]
  • [ 1007881-98-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 2058 - 2073
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