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[ CAS No. 1198-30-7 ] {[proInfo.proName]}

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Chemical Structure| 1198-30-7
Chemical Structure| 1198-30-7
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Product Details of [ 1198-30-7 ]

CAS No. :1198-30-7 MDL No. :MFCD00134166
Formula : C10H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :HJHXYSBRTVFEDD-UHFFFAOYSA-N
M.W : 154.17 Pubchem ID :306057
Synonyms :

Calculated chemistry of [ 1198-30-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.46
TPSA : 36.68 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) : -5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 2.3
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 0.87
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 1.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.86
Solubility : 0.212 mg/ml ; 0.00138 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.302 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0261 mg/ml ; 0.000169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 1198-30-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1198-30-7 ]

* 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.

  • Upstream synthesis route of [ 1198-30-7 ]
  • Downstream synthetic route of [ 1198-30-7 ]

[ 1198-30-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 1198-30-7 ]
  • [ 75-16-1 ]
  • [ 58022-21-2 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: at 0℃; for 3 h;
Stage #2: With ammonium chloride In tetrahydrofuran; diethyl ether at 20℃; for 3 h;
A solution of isoquinoline-1-carbonitrile (Intemediate H1) (commercially available from Aldrich) (4.40 g, 28.5 mmol) in THF at 0° C. was treated with methylmagnesium bromide (20 mL, of a 3M soln in ether) for 3 h. (see procedure found in Vacher, B. et al J. Med. Chem. 1998 41, 5070; incorporated herein by reference). The mixture was quenched with a sat. solution of NH4Cl and stirred for 3 h at rt. The aqueous layer was basified with NaOH and extracted with ethyl acetate. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel with 10percent ethyl acetate: hexane to give 1-isoquinolin-1-yl-ethanone (Intermediate H2) 3.65g (75percent). A mixture of 4-iodo-1-tritylimidazole (commercially available) (15.5 g, 35.4 mmol) in dichloromethane (80 mL) at 20° C. was treated with ethyl magnesium bromide (12.0 mL, 36 mmol, 3M in ether) and allowed to react for 1 h. A solution of 1-isoquinolin-1-yl-ethanone (Intermediate H2) (3.65 g, 21.3 mmol) in dichloromethane (20 mL) was added via addition funnel at 20° C. and stirred for 16 h. The mixture was quenched with sat. ammonium chloride (100 mL) and diluted with dichloromethane. The residue was isolated in an aqueous workup. The product was extracted with CH2Cl2 and purified by chromatography on silica gel with 5percent NH3-MeOH: CH2Cl2 to give 1-isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) as a solid. 1-Isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) was subjected to TFA: trifluoroacetic acid, Pd/C under hydrogen similar to the catalytic reduction procedure of Method D to remove the trityl group and produced 1-1H-imidazol-4-yl)-isoquinolin-1-yl ethanol (Intermediate H4). 1-1H-Imidazol-4-yl)-isoquinolin-1-yl ethanol (Intermediate H4). (21 mmol) in dichloromethane (100 mL) was treated with triethylamine (24.0 mL, 172 mmol) at 0° C. Methanesulfonyl chloride (6.1 mL, 75 mmol) was added via syringe and the mixture was stirred for 2 h. The mixture was subjected to an aqueous work-up. The crude material was purified by chromatography on silica gel with 20percent EtOAc: hexane to 5percent NH3-MeOH: dichloromethane to give 1-[1-(1-methanesulfonyl-1H-imidazol-4-yl)-vinyl]-isoquinoline (Intermediate H5) 3 g. 1-[1-(1-Methanesulfonyl-1H-imidazol-4-yl)-vinyl]-isoquinoline (Intermediate H5) was subjected to the catalytic reduction procedure found in Method D to produce 1-[1-(1-methanesulfonyl-1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H6). Methanesulfonyl-1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H6) in ethanol and 2M HCl was heated at reflux for 18 h. The mixture was cooled to rt and basified with NaOH solid. The aqueous layer was extracted with isopropanol:chloroform (3:1). The organic fractions were dried over MgSO4, filtered and concentrated onto silica gel. The product, 1-[1-(1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H7) was eluted from a column of silica gel with 3 to 5percent NH3-MeOH: CH2Cl2. 1-[1-(1H-Imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H7) was subjected to the appropriate process steps in Method A to produce 4-(1-isoquinolin-1-yl-ethyl)-1,3-dihydro-imidazole-2-thione (Compound 13) 1H NMR (300 MHz, DMSO-d6): δ11.9 (s, 1H), 11.6 (s, 1H), 8.42 (dd, J=5.4, 2.7 Hz, 1H), 8.31 (d, J=8.1 Hz, 1H), 7.96 (d, J=8.1 Hz, 1H), 7.78-7.64 (m, 3H), 6.40 (s, 1H), 5.0 (q, J=6.9 Hz, 1H), 1.59 (d, J=6.9 Hz, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2393 - 2412
[2] Patent: US2006/69143, 2006, A1, . Location in patent: Page/Page column 22-23
  • 2
  • [ 1198-30-7 ]
  • [ 917-64-6 ]
  • [ 58022-21-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1997, vol. 32, # 5, p. 397 - 408
[2] Chemische Berichte, 1913, vol. 46, p. 2931
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 738
  • 3
  • [ 1198-30-7 ]
  • [ 58022-21-2 ]
YieldReaction ConditionsOperation in experiment
62% With methylmagnesium bromide In tetrahydrofuran Example 232
4-Amino-6-chloro-2-(1-(1-isoquinolyl)ethyl)thio-pyrimidine (Cpd #232)
Methyl magnesium bromide in ether (8.1 ml, 24.3 mmole) is dissolved in 16 ml tetrahydrofuran in an oven dried 100 ml two neck round bottom flask under nitrogen.
The solution is cooled to 0° C., is diluted with 8 ml diethyl ether, and is treated with 1-isoquinoline carbonitrile (3.0 g, 19.5 mmole).
The reaction is warmed to reflux for one hour, is cooled to 0° C., and is quenched with 20 ml 6 M hydrochloric acid.
The reaction mixture is warmed to 50° C. for two hours, is cooled, and is poured into 75 ml 2N sodium hydroxide.
The mixture is extracted with 3*80 ml ethyl acetate and the combined organics are dried over potassium carbonate.
The dried organics are concentrated in vacuo to a crude amber oil.
The crude material is chromatographed over 150 g silica gel (230-400 mesh), eluding with 10percent acetone/hexane, while collecting 22 ml fractions.
Fractions 16-26 are combined and concentrated to provide 2.1 g (62percent) of 1-acetylisoquinoline.
H-NMR (CDCl3, TMS): δ 2.87 (s,3), 7.64-7.73 (m, 2), 7.80 (d, J=5.5 Hz, 1), 7.83-7.88 (m, 1), 8.58 (d, J=5.5 Hz, 1), 8.94-8.98 (m, 1) ppm. 13 C-NMR (CDCl3): δ 28.6; 124.6; 125.7; 126.9; 127.0; 129.1; 130.3; 137.0; 141.0; 152.8; 202.7 ppm. TLC (silica gel-60, F-254): Rf =0.45, 20percent acetone/hexane.
Infrared (ν max, liquid): 3054, 1694, 1582, 1358, 1239, 1133, 940, 833, 750 cm-1.
Mass Spectrum, [M/Z](relative intensity): [171](63). Analysis: Calculated for C11 H9 NO: C, 77.17; H,5.30; N,8.18. Found: C, 77.09; H,5.33; N,8.10.
Reference: [1] Patent: US6043248, 2000, A,
  • 4
  • [ 1198-30-7 ]
  • [ 74-88-4 ]
  • [ 58022-21-2 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, # 2, p. 476 - 481
  • 5
  • [ 1198-30-7 ]
  • [ 486-73-7 ]
Reference: [1] Chemische Berichte, 1913, vol. 46, p. 2927
[2] Chemische Berichte, 1913, vol. 46, p. 2927
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