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[ CAS No. 6127-17-9 ] {[proInfo.proName]}

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Chemical Structure| 6127-17-9
Chemical Structure| 6127-17-9
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Product Details of [ 6127-17-9 ]

CAS No. :6127-17-9 MDL No. :MFCD09027716
Formula : C9H8ClN Boiling Point : -
Linear Structure Formula :- InChI Key :NNJZGKJLPCDYQB-UHFFFAOYSA-N
M.W :165.62 Pubchem ID :271553
Synonyms :

Calculated chemistry of [ 6127-17-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.27
TPSA : 15.79 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) : -5.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 3.08
Log Po/w (WLOGP) : 3.13
Log Po/w (MLOGP) : 2.46
Log Po/w (SILICOS-IT) : 3.63
Consensus Log Po/w : 2.87

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.41
Solubility : 0.064 mg/ml ; 0.000387 mol/l
Class : Soluble
Log S (Ali) : -3.08
Solubility : 0.138 mg/ml ; 0.000834 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.28
Solubility : 0.00873 mg/ml ; 0.0000527 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 6127-17-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6127-17-9 ]

* 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 [ 6127-17-9 ]
  • Downstream synthetic route of [ 6127-17-9 ]

[ 6127-17-9 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 163688-23-1 ]
  • [ 6127-17-9 ]
YieldReaction ConditionsOperation in experiment
77% With trifluoroacetic acid In dichloromethane at 20℃; for 2 h; Inert atmosphere To a stirred solution of compound 5 (2.3 g, 8.12 mmol) in CH2C12 (40 mL) under inert atmosphere was added TFA (7.5 mL) at RT. The reaction mixture was stirred for 2 h. The reaction progress was monitored by TLC; after reaction completion, the reaction mixture was quenched with water (40 mL) and extracted with CH2C12 (2 x 50 mL). The combined organic extracts were washed with saturated NaHCO3 solution (40 mL), brine solution (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude material. The crude material was recrystallized with 5percent EtOAc/ hexanes to afford compound 6 (1 g, 77percent) as an off-white solid. 1H NMR (500 MHz, DMSO-d6): ö 11.02 (br s, 1H), 7.36 (d, J= 8.0 Hz, 1H), 7.25 (s, 1H), 6.90 (d, J= 8.5 Hz, 1H), 6.11 (s, 1H), 2.34 (s, 3H); LC-MS: 93.5percent; (M-H) Found=164; (column: X Bridge C-18,50 x 3.0 mm, 3.5 tm); RT 3.99 mm. 5 mMNH4OAc: ACN; 0.8 mL/min).
Reference: [1] Patent: WO2015/48301, 2015, A1, . Location in patent: Paragraph 00441
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 8, p. 2684 - 2690
  • 2
  • [ 53590-58-2 ]
  • [ 6127-17-9 ]
YieldReaction ConditionsOperation in experiment
27%
Stage #1: With triethylsilane; trifluoroacetic acid In 1,2-dichloro-ethane at 65℃; for 0.0833333 h;
Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane
A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C.
After 5 min, the reaction mixture was cooled to room temperature and quenched with water.
The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32percent).
The aqueous layer was extracted with tert-butyl methyl ether (3*200 ml).
The combined organic layers were dried over sodium sulfate and concentrated in vacuo.
The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27percent) as a white solid.
MS m/e (percent): 164 (M-H+, 100).
27% With triethylsilane; trifluoroacetic acid In 1,2-dichloro-ethane at 65℃; for 0.0833333 h; A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C.
After 5 min, the reaction mixture was cooled to room temperature and quenched with water.
The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32percent).
The aqueous layer was extracted with tert-butyl methyl ether (3*200 ml).
The combined organic layers were dried over sodium sulfate and concentrated in vacuo.
The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27percent) as a white solid.
MS m/e (percent): 164 (M-H+, 100).
27%
Stage #1: With triethylsilane; trifluoroacetic acid In 1,2-dichloro-ethane at 65℃; for 0.0833333 h;
Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane at 20℃;
A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C.
After 5 min, the reaction mixture was cooled to room temperature and quenched with water.
The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32percent).
The aqueous layer was extracted with tert-butyl methyl ether (3*200 ml).
The combined organic layers were dried over sodium sulfate and concentrated in vacuo.
The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27percent) as a white solid.
MS m/e (percent): 164 (M-H+, 100).
Reference: [1] Patent: US2007/27173, 2007, A1, . Location in patent: Page/Page column 112
[2] Patent: US2008/161315, 2008, A1, . Location in patent: Page/Page column 15
[3] Patent: US2007/27163, 2007, A1, . Location in patent: Page/Page column 22
  • 3
  • [ 6127-13-5 ]
  • [ 6127-17-9 ]
Reference: [1] Patent: US2018/305353, 2018, A1, . Location in patent: Paragraph 0892-0894
  • 4
  • [ 37629-52-0 ]
  • [ 6127-17-9 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 26, p. 5712 - 5715
  • 5
  • [ 2312-23-4 ]
  • [ 6127-17-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 135 - 158
  • 6
  • [ 67175-12-6 ]
  • [ 6127-17-9 ]
  • [ 6127-16-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 135 - 158
  • 7
  • [ 95-79-4 ]
  • [ 6127-17-9 ]
Reference: [1] Patent: WO2015/48301, 2015, A1,
  • 8
  • [ 876353-89-8 ]
  • [ 6127-17-9 ]
Reference: [1] Patent: WO2015/48301, 2015, A1,
  • 9
  • [ 89-61-2 ]
  • [ 6127-17-9 ]
Reference: [1] Patent: US2018/305353, 2018, A1,
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