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Product Details of [ 39885-08-0 ]

CAS No. :39885-08-0 MDL No. :MFCD09029932
Formula : C7H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :YKQICINWSAISBB-UHFFFAOYSA-N
M.W : 157.60 Pubchem ID :21925574
Synonyms :

Calculated chemistry of [ 39885-08-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.98
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 1.48
Log Po/w (SILICOS-IT) : 1.6
Consensus Log Po/w : 1.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.99
Solubility : 1.62 mg/ml ; 0.0103 mol/l
Class : Very soluble
Log S (Ali) : -1.83
Solubility : 2.33 mg/ml ; 0.0148 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.47
Solubility : 0.533 mg/ml ; 0.00338 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.02

Safety of [ 39885-08-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 39885-08-0 ]

* 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 [ 39885-08-0 ]
  • Downstream synthetic route of [ 39885-08-0 ]

[ 39885-08-0 ] Synthesis Path-Upstream   1~5

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  • [ 39885-08-0 ]
  • [ 4964-69-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8966 - 8970
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  • [ 35490-90-5 ]
YieldReaction ConditionsOperation in experiment
96% With manganese(IV) oxide In diethyl ether for 0.5 h; To prepare this compound, manganese dioxide (13.6 g, 157 mmol) was added to a solution of 2-(amino-6-chlorophenyl)methanol (2.75 g, 17.5 mmol) in 150 mL diethyl ether. The mixture was stirred for 0.5 hours then filtered through celite and rinsed with ethyl acetate. The filtrate was concentrated under reduced pressure to afford 2.62 g(96percent) of 2-amino-6-chlorobenzaldehyde.
85% With manganese(IV) oxide In dichloromethane at 20℃; for 23 h; Inert atmosphere General procedure: To a solution of 1a (1.2 g, 7.61 mmol) in CH2Cl2 (20 mL) was added MnO2 (2.6 g, 30.1 mmol) and stirred at rt under an Ar atmosphere. After 23 h with stirring, the reaction mixture was filtrated and evaporated. The residue was crystallized from AcOEt to give 7a (1.0 g, 85percent) as a yellow needle crystal. Mp 96–97 °C. IR (KBr): 3422, 3315, 1650, 1624, 1542, 1398, 1234, 919, 772 cm−1. 1H NMR (400 MHz, CD3OD) δ: 6.60 (1H, dd, J = 0.8, 7.6 Hz), 6.68 (1H, td, J = 0.8, 8.4 Hz), 7.18 (1H, dd, J = 7.6, 8.4 Hz), 10.41 (1H, d, J = 0.8 Hz). 13C NMR (100 MHz, CD3OD) δ: 114.6, 117.0, 117.5, 136.7, 140.2, 154.6, 193.3. HRMS (EI) Calcd for C7H6ClNO [M]+: 155.0138. Found: 155.0141.
10% With manganese(IV) oxide In diethyl ether at 20℃; for 6 h; 2.30 g (14.6 mmol) of (2-amino-6-chlorophenyl)methanol prepared in step 1, MnO2 (10 equivalent), and diethylether (50 mL) were mixed together, which was stirred at room temperature for 6 hours.
The reaction mixture was filtered with celite pad, and concentrated under reduced pressure.
The residue was separated by column chromatography (SiO2, eluent:
hexane/CH2Cl2, 5/1->CH2Cl2) to give 2.27 g of the target compound 2-amino-6-chlorobenzaldehyde as a yellow solid (14.6 mmol, yield: 10percent).
1H NMR(300 MHz, CDCl3) δ 10.48 (s, 1H) , 7.17 (t, J=8.2 Hz, 1H), 6.67 (d, J=7.7 Hz, 1H), 6.54 (d, J=8.4 Hz, 1H) , 6.48 (br s, 2H).
Reference: [1] Patent: WO2006/10142, 2006, A2, . Location in patent: Page/Page column 70; 71
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[3] ChemistryOpen, 2015, vol. 4, # 2, p. 107 - 110
[4] Patent: US2018/105527, 2018, A1, . Location in patent: Paragraph 0786-0788
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8966 - 8970
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YieldReaction ConditionsOperation in experiment
95% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Dissolves 50.0 g (286 mmol) of 2-amino-6chlorophenyl acid in 300 ml of anhydrous THF (Tetrahydrofuran)(2-Amino-6-chlorobenzoic acid) mixture, cooling the solution to 0 ~ 10 °C,Add 450ml of 1.0M lithium aluminum hydride THF solution,The reaction mixture was allowed to warm to room temperature and then stirred at room temperature overnight.300 ml of 10percent NaOH aqueous solution was added to the reaction mixture,The organic phase was separated and washed with ethyl acetate and water. After drying with magnesium sulfate,The solvent was removed in vacuo to give 42 g (270 mmol, 95percent) of the product as a yellow solid.No further purification.
88% With borane-THF In tetrahydrofuran at 0 - 30℃; for 1.66667 h; Inert atmosphere General procedure: To a solution of 6-chloroanthranilic acid (1.5 g, 8.74 mmol) in THF (5 mL) was added dropwise 1.08 M borane–tetrahydrofuran complex in THF (24.3 mL, 26.2 mmol) at 0 °C under an Ar atmosphere for 10 min. After 1.5 h with stirring at 30 °C, the solution was cooled at 0 °C, added aqueous THF (THF/H2O = 1:1, 60 mL) and potassium carbonate, and extracted with diethyl ether three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was crystallized from AcOEt to give 1a (1.2 g, 88percent) as a white needle crystal. Mp 76–78 °C. IR (KBr): 3388, 3107, 1451, 1004, 780 cm−1. 1H NMR (300 MHz, CDCl3) δ: 4.29 (2H, br s), 4.86 (2H, s), 6.57 (1H, dd, J = 0.9, 8.1 Hz), 6.77 (1H, dd, J = 0.9, 7.8 Hz), 7.00 (1H, t, J = 8.1 Hz), a proton (OH) was not observed. 13C NMR (75 MHz, CDCl3) δ: 59.4, 114.6, 119.1, 122.0, 129.6, 134.1, 147.9. HRMS (EI) Calcd for C7H8ClNO [M]+: 157.0294. Found: 157.0293.
75% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12.1667 h; 3.43 g (20.0 mmol) of 2-amino-6-chlorobenzoic acid was dissolved in anhydrous THF 30 mL), to which LiAlH4 (1.5 equivalent) was slowly added at room temperature for 10 minutes, followed by stirring for 12 hours. Diethylether (40 mL) and water (5 mL) were added thereto. The reaction mixture was dried (MgSO4) and concentrated under reduced pressure. The residue was separated by column chromatography (SiO2, eluent: CH2Cl2/ethyl acetate, 5/1->CH2Cl2/ethylacetate, 2/1) to give 2.36 g of the target compound (2-amino-6-chlorophenyl)methanol as a pale yellow solid (15.0 mmol, yield: 75percent). (0785) 1H NMR(300 MHz, CDCl3) δ 7.01 (t, J=8.0 Hz, 1H), 6.76 (d, J=7.9 Hz, 1H), 6.58 (d, J=8.0 Hz, 1H), 4.89 (s, 2H), 4.30 (br s, 2H), 1.66 (br s, 1H).
61%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h;
Stage #2: With methanol In tetrahydrofuran; ethyl acetate at 0℃;
To prepare this compound, lithium aluminum hydride (3.3 g, 88 mmol) was added in three portions to a suspension of 2-amino-6-chlorobenzoic acid (5.0 g, 29 mmol) in THF (145 mL) at 0 °C. That reaction was allowed to warm to room temperature and was stirred for 2 hours. Then the reaction was quenched slowly with ethyl acetate/methanol while cooling in an ice bath. That quenched suspension was filtered, washed with ethyl acetate/methanol and filtered. The filtrate was concentrated under reduced pressure and the resultant material was purified by flash chromatography (4:1 hexanes:ethyl acetate) to afford 2.75 g (61percent) of 2-(amino-6-chlorophenyl)methanol.
52% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16 h; To a suspension of lithium aluminium hydride(1.1g, 29.1 mmol) in tetrahydrofuran (150 ml) was added 2-amino-6-chlorobenzoic acid (5g, 29.1 mmol) at 0C. The mixture was stirred at room temperature for 16h. Then, the reaction mixture was quenched with sodium sulfate decahydrate (3 gh) and brine ( 10 ml) and filtrated through a pad of celite. The organic layer was concentrated in vacuo and the residue was chromatographed on a column of silica gel eluting with ethylacetate/hexane (1:2) to give 2.4 g (52percent) of the title compound as a colorless oil.1H-NMR (CDCL3) d: 7.01 (1 H, dd, J=7.9, 8.1Hz), 6.76 (1 H, d, J= 7.9 Hz), 6.58 (1 H, D, J=8.1 Hz) 4.88(2H, S). Signals due to NH2 and OH were not observed.
20 g With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Cooling with ice In a 500 mL two-necked round bottom flask, 1-1 (25.0 g, 143 mmol) was dissolved in 120 mL anhydrous THF. The solution was cooled in an ice water bath, and then 215 mL of a 1.0 M lithium aluminum hydride (LAH) THF solution was added dropwise. After all the LAH had been added, the reaction mixture was warmed to room temperature and stirred at room temperature overnight. 10 mL of water was added to the reaction mixture followed by 7 g of 15percent NaOH. An additional 20 g of water was added to the reaction mixture. The organic THF phase was decanted and ethyl acetate was added as a solid. It was added to 200 mL and stirred, and the ethyl acetate organic portion and the THF portion were combined and a Na 2 SO 4 desiccant was added. Filter and evaporate the mixture.Yield 20g of yellow solid,No further purification was carried out for the next reaction.

Reference: [1] Patent: CN107722059, 2018, A, . Location in patent: Paragraph 0094; 0097; 0098; 0099
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2080 - 2092
[4] Patent: US2018/105527, 2018, A1, . Location in patent: Paragraph 0783-0785
[5] Patent: WO2006/10142, 2006, A2, . Location in patent: Page/Page column 70
[6] Patent: WO2005/49608, 2005, A1, . Location in patent: Page/Page column 52-53
[7] Patent: WO2012/148511, 2012, A1, . Location in patent: Page/Page column 53
[8] Patent: US2013/32785, 2013, A1, . Location in patent: Page/Page column
[9] Patent: EP2554548, 2013, A1, . Location in patent: Paragraph 0122-0123
[10] Angewandte Chemie, International Edition, 2014, vol. 53, # 36, p. 9603 - 9607,5[11] Angewandte Chemie, 2014, vol. 126, # 36, p. 9757 - 9761,5
[12] Organic Letters, 2015, vol. 17, # 19, p. 4750 - 4753
[13] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8966 - 8970
[14] Organic Letters, 2017, vol. 19, # 19, p. 5236 - 5239
[15] Organic and Biomolecular Chemistry, 2018, vol. 16, # 12, p. 2039 - 2042
[16] Organic Letters, 2018, vol. 20, # 10, p. 2939 - 2943
[17] Patent: CN108659053, 2018, A, . Location in patent: Paragraph 0084; 0085; 0086; 0087
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Reference: [1] Patent: US2012/181511, 2012, A1,
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  • [ 39885-08-0 ]
Reference: [1] Patent: US2018/105527, 2018, A1,
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