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[ CAS No. 7211-54-3 ] {[proInfo.proName]}

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Chemical Structure| 7211-54-3
Chemical Structure| 7211-54-3
Structure of 7211-54-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7211-54-3 ]

CAS No. :7211-54-3 MDL No. :MFCD00137453
Formula : C3H10ClNS Boiling Point : -
Linear Structure Formula :- InChI Key :GMEDUXHKSSWXSL-UHFFFAOYSA-N
M.W : 127.64 Pubchem ID :197870
Synonyms :

Calculated chemistry of [ 7211-54-3 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.14
TPSA : 64.82 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.73
Log Po/w (WLOGP) : 1.07
Log Po/w (MLOGP) : 0.75
Log Po/w (SILICOS-IT) : 0.15
Consensus Log Po/w : 0.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.96
Solubility : 14.0 mg/ml ; 0.11 mol/l
Class : Very soluble
Log S (Ali) : -1.67
Solubility : 2.73 mg/ml ; 0.0214 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.75
Solubility : 22.7 mg/ml ; 0.178 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.32

Safety of [ 7211-54-3 ]

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

Application In Synthesis of [ 7211-54-3 ]

* 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.

  • Downstream synthetic route of [ 7211-54-3 ]

[ 7211-54-3 ] Synthesis Path-Downstream   1~68

  • 1
  • [ 17240-25-4 ]
  • [ 7211-54-3 ]
  • 3-(5,6-dihydro-4<i>H</i>-[1,3]oxazin-2-ylamino)-propane-1-thiol [ No CAS ]
  • 2
  • [ 17240-25-4 ]
  • [ 7211-54-3 ]
  • [ 30477-24-8 ]
  • 3
  • [ 3458-28-4 ]
  • [ 7211-54-3 ]
  • [ 93284-19-6 ]
  • 4
  • [ 5328-37-0 ]
  • [ 7211-54-3 ]
  • [ 92673-65-9 ]
  • 5
  • [ 50-99-7 ]
  • [ 7211-54-3 ]
  • [ 93284-19-6 ]
  • 6
  • [ 59-23-4 ]
  • [ 7211-54-3 ]
  • [ 93284-19-6 ]
  • 7
  • [ 7211-54-3 ]
  • [ 98-88-4 ]
  • [ 88313-86-4 ]
  • 8
  • [ 7211-54-3 ]
  • [ 2243-83-6 ]
  • 3-β-Naphthoylmercapto-propylamin [ No CAS ]
  • 9
  • [ 90-46-0 ]
  • [ 7211-54-3 ]
  • [ 78264-32-1 ]
  • 10
  • [ 50-00-0 ]
  • [ 7211-54-3 ]
  • [ 79128-34-0 ]
  • 11
  • [ 107409-98-3 ]
  • [ 7211-54-3 ]
  • [ 78264-37-6 ]
  • 12
  • [ 112-31-2 ]
  • [ 7211-54-3 ]
  • nonyl-2 perhydrothiazine-1,3 chlorhydrate [ No CAS ]
  • 13
  • [ 110-62-3 ]
  • [ 7211-54-3 ]
  • butyl-2 perhydrothiazine-1,3 chlorhydrate [ No CAS ]
  • 14
  • [ 3132-99-8 ]
  • [ 7211-54-3 ]
  • 2-(3'-bromophenyl)-1,3-perhydrothiazine hydrochloride [ No CAS ]
  • 15
  • [ 123-15-9 ]
  • [ 7211-54-3 ]
  • (methyl-1' butyl)-2 perhydrothiazine-1,3 chlorhydrate [ No CAS ]
  • 16
  • [ 96460-00-3 ]
  • [ 7211-54-3 ]
  • [ 78264-34-3 ]
  • 17
  • [ 13209-86-4 ]
  • [ 7211-54-3 ]
  • [ 78264-33-2 ]
  • 18
  • [ 7211-54-3 ]
  • [ 38585-62-5 ]
  • 3-<(5-Methylimidazol-4-yl)methylthio>-1-propylamine-Dihydrobromid [ No CAS ]
  • 19
  • [ 7211-54-3 ]
  • [ 104-87-0 ]
  • 2-p-Tolyl-[1,3]thiazinane; hydrochloride [ No CAS ]
  • 20
  • [ 7211-54-3 ]
  • [ 459-57-4 ]
  • 2-(4'-fluorophenyl)-1,3-perhydrothiazine hydrochloride [ No CAS ]
  • 21
  • [ 7211-54-3 ]
  • [ 104-88-1 ]
  • 2-(4-Chloro-phenyl)-[1,3]thiazinane; hydrochloride [ No CAS ]
  • 22
  • [ 7211-54-3 ]
  • [ 152810-85-0 ]
  • [ 78264-36-5 ]
  • 23
  • [ 7211-54-3 ]
  • [ 13209-87-5 ]
  • [ 78264-35-4 ]
  • 24
  • [ 7211-54-3 ]
  • [ 100-52-7 ]
  • phenyl-2 perhydrothiazine-1,3 chlorhydrate [ No CAS ]
  • 25
  • [ 7211-54-3 ]
  • [ 123-11-5 ]
  • 2-(4-Methoxy-phenyl)-[1,3]thiazinane; hydrochloride [ No CAS ]
  • 27
  • [ 7211-54-3 ]
  • [ 123-38-6 ]
  • ethyl-2 perhydrothiazine-1,3 chlorhydrate [ No CAS ]
  • 28
  • [ 7211-54-3 ]
  • [ 123-72-8 ]
  • propyl-2 perhydrothiazine-1,3 chlorhydrate [ No CAS ]
  • 29
  • [ 7211-54-3 ]
  • [ 78-84-2 ]
  • isopropyl-2 perhydrothiazine-1,3 chlorhydrate [ No CAS ]
  • 30
  • [ 7211-54-3 ]
  • [ 529-20-4 ]
  • 2-o-Tolyl-[1,3]thiazinane; hydrochloride [ No CAS ]
  • 31
  • [ 7211-54-3 ]
  • [ 6287-38-3 ]
  • 2-(3,4-Dichloro-phenyl)-[1,3]thiazinane; hydrochloride [ No CAS ]
  • 32
  • [ 15047-09-3 ]
  • [ 7211-54-3 ]
  • 33
  • [ 126158-18-7 ]
  • [ 7211-54-3 ]
  • (3RS,4RS)-1-(4-methoxyphenyl)-4-(1,3-thiazan-2-yl)-3-phthalimidoazetidin-2-one [ No CAS ]
  • 34
  • <γ-mercapto-propyl>-phthalimide [ No CAS ]
  • [ 7211-54-3 ]
  • 35
  • [ 7211-54-3 ]
  • [ 125829-10-9 ]
  • 36
  • [ 7211-54-3 ]
  • [ 157825-86-0 ]
  • [ 31417-02-4 ]
  • 37
  • [ 5554-48-3 ]
  • [ 7211-54-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water; for 336h;Reflux; Inert atmosphere; 3-Aminopropanethiol hydrochloride (8).5; A suspension of 7 (7.70 g, 57.8 mmol) in cone. aq. HC1 (50 mL) was heated at reflux for 2 weeks under N2. After cooling to room temperature, the residual aq. HC1 was removed by vacuum distillation (P = 5 mmHg) under mild heating (60 C) for 1 h. The solid residue was suspended in a degassed solution of Et20/EtOH (9: 1, 50 mL) and stirred for 10 min at room temperature under argon, then poured into a coarse fritted Schlenk filter under argon and thoroughly washed with a degassed solution of Et20/EtOH (9: 1), to give a white solid, which was dried in the Schlenk filter under high vacuum overnight to yield the first crop of solid as a mixture of 8 and the corresponding disulfide (4.35 g). A second crop of solid was collected by filtration into a regular coarse fritted funnel under air to yield pure disulfide (38.0 mg). The overall yield4841-4125-8254.2 -52- Atty Dkt. No. 076333-0733 based on mass recovery was 64% (4.73 g) of a white, highly hygroscopic solid that requires storage in a vacuum dessicator containing drierite: Spectroscopic data for crop 1 [disulfide(57%) + 8 (43%)]: IR (ATR, neat) 2894 (br), 2965 (br), 1607, 1493 cm"1; major product (disulfide): 1H NMR (D20, 600 MHz) delta 3.14-3.10 (m, 2 H), 2.81 (t, 2 H, J= 7.1 Hz), 2.14- 2.07 (m, 2 H); 13C NMR (D20, 150 MHz) delta 40.9, 36.5, 28.8; minor product (8): 1H NMR (D20, 600 MHz) delta 3.14-3.10 (m, 2 H), 2.63 (t, 2 H, J= 7.0 Hz), 2.00-1.94 (m, 2 H); 13C NMR (DMSO-< , 150 MHz) delta 40.9, 33.4, 23.4.
  • 38
  • [ 114326-11-3 ]
  • [ 463-22-9 ]
  • [ 7211-54-3 ]
  • 39
  • [ 137048-10-3 ]
  • [ 7211-54-3 ]
  • 3-aminopropyl 4-amino thiobutyrate dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; ethanol; acetonitrile; Example 6--Preparation of 3-aminopropyl 4-amino thiobutyrate dihydrochloride A suspension of 12.8 g (0.1 mole) of 3-mercapto propylamine hydrochloride and 11.58 g (0.1 mole) of 4-amino butyric acid chloride hydrochloride in 75 cm3 of anhydrous acetonitrile is stirred under an inert atmosphere and heated for 4 hours at reflux. After cooling to ambient temperature, the crude thioester is drained, washed with iced methanol and then recrystallized in a 75/25 ethanol/methanol mixture. After drying under a vacuum at 50 C., 17.5 g of 3-aminopropyl 4-amino thiobutyrate dihydrochloride in the form of a white solid whose melting point is 205 C. are obtained. The NMR1 H 80 MHz spectrum conforms to the expected structure.
  • 40
  • 3-chloro-2-hydroxymethylpryridine [ No CAS ]
  • [ 7211-54-3 ]
  • [ 13623-94-4 ]
  • 1-Nitro-2-(2-propynylamino)-2-{3-[(3-chloro-pyridin-2-yl)methylthio]propylamino}ethylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hydrogen bromide; EXAMPLE 11 1-Nitro-2-(2-propynylamino)-2-{3-[(3-chloro-2-pyridyl)methylthio]propylamino}ethylene When 3-chloro-2-hydroxymethylpryridine is reacted with 3-mercaptopropylamine hydrochloride [prepared according to the procedure described in J. Org. Chem., 27, 2846 (1962)] in aqueous hydrobromic acid (48%) and the resultant amine successively treated with 1,1-bis(methylthio)-2-nitroethylene and excess propargylamine according to the general procedure of Example 1, the title compound is produced.
  • 41
  • sodium acetylmethylphosphinate [ No CAS ]
  • [ 7211-54-3 ]
  • sodium methyl(2-methylperhydro-1,3-thiazin-2-yl)phosphinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; EXAMPLE 33 Sodium methyl(2-methylperhydro-1,3-thiazin-2-yl)phosphinate <strong>[7211-54-3]3-Mercaptopropylamine hydrochloride</strong> (2.6 g, 0.02 mol) was stirred in ethanol (25 ml) with sodium hydroxide (0.8 g, 0.02 mol) for about 11/2 hours and then filtered through Kieselguhr. This solution was added to a stirred slurry of sodium acetylmethylphosphinate (2.9 g, 0.02 mol) in ethanol (20 ml) and the mixture stirred overnight. The solution was evaporated under reduced pressure, giving a white foamy solid which was dissolved in ethanol, precipitated with dry ether and filtered. The filtrate was evaporated to a foamed solid, which was dried in vacuo giving 2.5 g, 58% of product, mp 155-160. N.m.r. was consistent with the desired product.
  • 42
  • [ 7211-54-3 ]
  • [ 79-44-7 ]
  • 1,1-Dimethyl-3-(mercaptopropyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; triethylamine; In dichloromethane; EXAMPLE 2 1,1-Dimethyl-3-(mercaptopropyl)urea (2) 5 g of 1A was treated with sodium methoxide as described in Example 1. The methanol was evaporated under reduced pressure. 4 g of dimethylcarbamoyl chloride, 6 g of triethylamine and 30 ml of methylene chloride were added over 10 minutes at 0 C. under nitrogen. The resulting mixture was held overnight at room temperature, then was poured into a 2% hydrochloric acid solution saturated with sodium chloride. Purification of the organic phase over silica gel gave 2.
  • 43
  • [ 7211-54-3 ]
  • [ 98-88-4 ]
  • N-benzoyl-3-aminopropanethiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 4 N-(3-Mercaptopropyl)benzamide (4) was prepared from 1A and benzoyl chloride by the procedures described in Examples 1-3.
  • 44
  • [ 98156-90-2 ]
  • [ 7211-54-3 ]
  • [ 98-09-9 ]
  • [ 98156-91-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium methylate; triethylamine; triphenylphosphine; In methanol; dichloromethane; water; EXAMPLE 3 N-(3-Mercaptopropyl)benzenesulfonamide (3) 5 g of 1A was treated with sodium methoxide as described in Example 1. The solvent was evaporated. The residue was mixed with 60 ml of methylene chloride and 6 g of triethylamine, then a solution of 7 g of phenylsulfonyl chloride in 40 ml of methylene chloride was added drop-by-drop over 30 minutes, at 0 C. The resulting mixture was held at room temperature for 20 minutes, and the solid product was separated, washed with 2% hydrochloric acid and triturated with diethyl ether to give bis(3-(phenylsulfonylamino)propyl)disulfide (3A). 3.1 g of 3A was treated with a mixture of 2.5 g of triphenylphosphine, 2.5 g of water, 50 ml of methanol and 10 drops of 10% hydrochloric acid. The resulting mixture was refluxed for 11 hours, then most of the solvent was evaporated and the residue was extracted with methylene chloride. The extract was washed with water, the solvent was evaporated and the residue was chromatographed over silica gel to give 3.
  • 45
  • [ 7211-54-3 ]
  • [ 18370-84-8 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; sodium; acetic anhydride; In methanol; EXAMPLE 1 N-(3-Mercaptopropyl)acetamide (1) Sodium methoxide (1 g of sodium in 25 ml of methanol) was added to 5 g of the hydrochloride salt of 3-aminopropanethiol (1A), and the mixture was allowed to cool. Then 5 g of acetic anhydride was added and the mixture was stirred for 30 minutes. Ether was added, the resulting mixture was filtered and the filtrate was evaporated to dryness (90 C.). The residue was extracted with methylene chloride, and the extract was evaporated to dryness. Purification of the residue on an alumina column gave 1, as a oil.
  • 46
  • [ 7211-54-3 ]
  • [ 78441-69-7 ]
  • [ 55904-83-1 ]
  • 3-{3-[(2-Dimethylaminomethyl-4-thiazolyl)methylthio]propylamino}-4-methylamino-1,2,5-thiadiazole 1,1-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hydrogen bromide; EXAMPLE 40 3-{3-[(2-Dimethylaminomethyl-4-thiazolyl)methylthio]propylamino}-4-methylamino-1,2,5-thiadiazole 1,1-dioxide When 2-dimethylaminomethyl-4-hydroxymethylthiazole [prepared in Example 34, Step D] is reacted with 3-mercaptopropylamine hydrochloride [prepared according to the procedure described in J. Org. Chem., 27, 2846 (1962)] in aqueous hydrobromic acid (48%), and the resultant amine is successively treated with 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide and excess methylamine as in the general procedure of Example 31, the title compound is produced.
In hydrogen bromide; EXAMPLE 40 3-{3 -[(2-Dimethylaminomethyl-4-thiazolyl)methylthio]propylamino}-4-methylamino-1,2,5-thiadiazole 1,1-dioxide When 2-dimethylaminomethyl-4-hydroxymethylthiazole [prepared in Example 34, Step D] is reacted with 3-mercaptopropylamine hydrochloride [prepared according to the procedure described in J. Org. Chem., 27, 2846 (1962)] in aqueous hydrobromic acid (48%), and the resultant amine is successively treated with 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide and excess methylamine as in the general procedure of Example 31, the title compound is produced.
  • 47
  • [ 7211-54-3 ]
  • [ 38585-62-5 ]
  • 4-methyl-5-[(3-aminopropyl)thiomethyl]imidazole dihydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hydrogen bromide; i. A solution of homocysteamine hydrochloride (22.0 g.) and <strong>[38585-62-5]4-hydroxymethyl-5-methylimidazole hydrochloride</strong> (25.6 g.) in aqueous hydrobromic acid (500 ml.) was heated under reflux for 1 hour. Concentration under reduced pressure, followed by recrystallisation from methanol-isopropyl alcohol afforded 4-methyl-5-[(3-aminopropyl)thiomethyl]imidazole dihydrobromide (24.5 g.), m.p. 200.5-202.5.
  • 48
  • [ 89-51-0 ]
  • [ 7211-54-3 ]
  • [ 67755-06-0 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; toluene-4-sulfonic acid; In ethanol; chloroform; 1,2-dichloro-benzene; EXAMPLE 3 STR46 In 20 ml. of o-dichlorobenzene were dissolved 7.2 g. of 2-carboxymethylbenzoic acid and 5.2 g. of 3-aminopropanethiol hydrochloride and after adding 6.6 g. of sodium acetate to the solution, the resultant mixture was refluxed for 3 hours. The precipitates thus formed were filtered off and 3 g. of p-toluenesulfonic acid was added to the filtrate followed by refluxing for one hour. After the reaction was over, the reaction mixture was cooled, applied to a silica gel column chromatography using 80 g. of silica gel, and purified by a mixture of ethanol and chloroform (1:99 by volume ratio). The fractions containing the desired product were collected, the solvent was distilled off, and the crude crystals obtained were recrystallized from ethanol to provide 3.0 g. of 6-oxo-3,4-dihydro-2H,6H-1,3-thiazino[3,2-b]isoquinoline. Melting point 85-86 C. Elemental analysis for C12 H11 NSO:
  • 49
  • [ 14542-12-2 ]
  • [ 7211-54-3 ]
  • [ 13623-94-4 ]
  • 1-Nitro-2-(2-propynylamino)-2-{3-[(thiazol-2-yl)methylthio]propylamino}ethylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hydrogen bromide; EXAMPLE 9 1-Nitro-2-(2-propynylamino)-2-{3-[(thiazol-2-yl)methylthio]propylamino}ethylene When 2-hydroxymethylthiazole is reacted with 3-mercaptopropylamine hydrochloride [prepared according to the procedure described in J. Org. Chem., 27, 2846 (1962)] in aqueous hydrobromic acid (48%) and the resultant amine successively treated with 1,1-bis(methylthio)-2-nitroethylene and excess propargylamine, the title compound is produced.
  • 50
  • aqueous potassium hydroxide [ No CAS ]
  • [ 59194-41-1 ]
  • [ 7211-54-3 ]
  • 10-(3-aminopropylthio)-8-chloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; hexane; dichloromethane; EXAMPLE 21 10-(3-Aminopropylthio)-8-chloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]naphthyridine A solution of 5.0 g (0.0188 mol) of the compound of Example 6, 3.3 g (0.02244 m) of 3-aminopropanethiol hydrochloride, 15 ml of 18.5% aqueous potassium hydroxide (0.05 m) and 30 ml of absolute ethanol is refluxed for one and a half hours. After evaporation of the solution, the residue is dissolved in methylene chloride and extracted with water. Evaporation of the methylene chloride solution gives the free base. Recrystallization of the product from hexane affords the title compound as a crystaline solid (3.2 g, 53%), m.p. 87-89 C. Analysis for: C16 H20 ClN3 S. Calculated: C, 59.70; H, 6.26; N, 13.05; S, 9.96. Found: C, 60.27; H, 6.40; N, 13.02; S, 9.95.
  • 51
  • [ 167633-99-0 ]
  • [ 7211-54-3 ]
  • 2-(pentafluoroethylcarbonylmethylene)-1,3-thiazinane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; hexane; ethyl acetate; EXAMPLE 6 3-Aminopropanethiol hydrochloride (2.5 g), 1-(pentafluoroethylcarbonyl)-2,2-diethoxy ethanol (5.0 g) and DBU (3.0 g) were refluxed in ethanol (50 ml) for 24 hours. After removal of the solvent under vacuum the residue was partitioned between dichloromethane (50 ml) and water (50 ml). The organic phase was washed twice with water (2 x 50 ml), dried, and the solvent removed under vacuum. Column chromatography using silica gel and hexane/ethyl acetate, 50/50, v/v, as eluent yielded 2-(pentafluoroethylcarbonylmethylene)-1,3-thiazinane as a white solid (1.6 g). mp 115C.
  • 52
  • nickel(II) nitrate hexahydrate [ No CAS ]
  • [ 7211-54-3 ]
  • [ 36530-26-4 ]
  • 53
  • iron(II) chloride tetrahydrate [ No CAS ]
  • [ 7211-54-3 ]
  • Fe3(S(CH2)3NH2)6(3+)*3Cl(1-)=Fe3(S(CH2)3NH2)6Cl3 [ No CAS ]
  • 54
  • rhodium(III) chloride trihydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 7211-54-3 ]
  • fac(S)-rhodium(III) 3-aminopropanethiolate dihydrate [ No CAS ]
  • 55
  • [ 84592-36-9 ]
  • [ 7211-54-3 ]
  • 3-aminopropyl-tert-butyl disulfide hydrochloride [ No CAS ]
  • 57
  • [ 1259977-93-9 ]
  • [ 7211-54-3 ]
  • [ 1259978-05-6 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 - 70℃; for 20h;Inert atmosphere; 2,3,4,5-Tetrahydro-10-benzyloxybenzo[¾]thieno[2,3- ]-l,5-thiazocin-6-one (9).; To a solution of 5 (300 mg, 0.901 mmol) in anhydrous, degassed DMF (7.5 mL) was added hydrochloride salt 8 (1.15 g, 3.88 mmol, 43%> purity) followed by degassed DBU (1.50 mL, 9.93 mmol) under argon. The reaction mixture was stirred at room temperature for 2 h, then warmed to 70 C and stirred for 18 h. After cooling to room temperature, the solution was diluted with EtOAc (30 mL) and washed with 2 M aq. HC1 (30 mL). The aqueous phase was extracted with EtOAc (3 x 30 mL) and the combined organic layers were washed with brine (1 x 150 mL), dried (MgS04) and concentrated to yield a yellow oil, which was dried under high vacuum to remove residual DMF. The residue was preloaded on Si02 and purified by chromatography on Si02 (hexanes to 5% MeOH in EtOAc) to give a yellow solid, which was suspended in Et20/MeOH (9: 1), filtered, triturated with Et20 and dried under high vacuum to yield 9 (133 mg, 42%) as a white solid: Mp 198-199 C; IR (ATR, neat) 3162, 3033, 2937, 1644, 1619, 1600, 1497, 1384, 1274, 1193 cm"1; 1H NMR (DMSO-d6, 600 MHz) delta 8.02 (bs, 1 H), 7.90-7.84 (m, 1 H), 7.51-7.45 (m, 2 H), 7.43-7.37 (m, 2 H), 7.36-7.31 (m, 1 H), 7.26- 7.19 (m, 2 H), 5.20 (s, 2 H), 3.50-3.43 (m, 2 H), 3.30-3.24 (m, 2 H), 1.92-1.89 (m, 2 H); 13C NMR (DMSO-d6, 150 MHz) delta 164.8, 156.4, 138.7, 136.9, 130.3, 128.5, 128.5, 127.9, 127.7, 127.4, 123.6, 117.3, 105.8, 69.6, 30.5, 27.4; MS (EI) m/z, 355 (M+, 100), 356 (23), 357 (12); HRMS (EI) m/z calcd for Ci9Hi7N02S2 355.0701, found 355.0689.
  • 59
  • C37H46ClN3O10 [ No CAS ]
  • [ 7211-54-3 ]
  • C68H98Cl2N6O14S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine; N,N-dimethyl-formamide; In dichloromethane; at 23℃; for 3h; To a solution of Compound 16 (156.3 mg, 0.21 mmol) in DCM (2.5 ml.) were added a suspension of 3-aminopropane-1 -thiol hydrochloride (44.8 mg, 0.26 mmol) in DCM (2.5 mL), triethylamine (58 mu, 0.34 mmol) and DMF (0.1 mL) at 23 C. The reaction mixture was stirred at 23 C for 3 h, diluted with H20 and extracted with DCM. The combined organic layers were dried over anhydrous Na2S04, filtered andconcentrated under vacuum. The residue obtained was purified in a system for flash chromatography (Si02, Hex:EtOAc mixtures) to afford pure Compound 17 (80 mg, 95%).1H NMR (300 MHz, CDCI3): delta 8.68 (d, J = 10.6 Hz, 1 H), 7.28 (t, J = 1 1.6 Hz, 1 H), 6.89 (t, J = 1 1 .5 Hz, 1 H), 6.76 (t, J = 9.6 Hz, 1 H), 6.65 (d, J = 9.1 Hz, 1 H), 6.13 (d, J = 1 1 .7 Hz, 1 H), 5.87-5.51 (m, 4H), 5.28 (d, J = 5.0 Hz, 1 H), 4.77 (q, J = 8.2 Hz, 1 H), 4.61 -4.39 (m, 2H), 4.29-4.00 (m, 1 H), 3.65 (s, 3H), 3.31 -3.18 (m, 2H), 2.98-2.77 (m, 1 H), 2.68 (t, J = 7.4 Hz, 2H), 2.55-2.22 (m, 6H), 2.04 (s, 3H), 2.00-1.80 (m, 2H), 1.83 (s, 3H), 1 .15 (d, J = 6.6 Hz, 3H), 1 .05 (s, 9H). ESI-MS m/z: Calcd. for C68H98Cl2N6Oi4S2: 1356.6. Found: 1357.3 (M+H)+.
  • 60
  • C37H47N3O10 [ No CAS ]
  • [ 7211-54-3 ]
  • C68H100N6O14S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In dichloromethane; at 23℃; for 7h; To a solution of Compound 29 (121.3 mg, 0.17 mmol), prepared as described in step (a) above, in DCM (2.5 mL) were added a suspension of 3-aminopropane-1 -thiol hydrochloride (37.2 mg, 0.29 mmol) in DCM (2.5 mL), DIPEA (59 mu, 0.34 mmol) and DMF (0.1 mL) at 23 C. The reaction mixture that was stirred at 23 C for 7 h, diluted with H20 and extracted with EtOAc. The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated under vacuum. The residue obtained was purified in a system for flash chromatography (Si02, Hex:EtOAc mixtures) to afford pure Compound 35 (40.5 mg, 37%).1H NMR (300 MHz, CDCI3): 58.63 (d, J= 10.6 Hz, 1 H), 7.34- 7.21 (m, 1H), 6.88 (t, J = 11.4 Hz, 1H), 6.76 (t, J = 9.6 Hz, 1H), 6.68 (d, J= 9.3 Hz, 1H), 6.13 (d, J= 11.6 Hz, 1 H), 5.7-5.67 (m, 3H), 5.66-5.48 (m, 3H), 4.81 (q, J = 8.1 Hz, 1 H), 4.66-4.50 (m, 1 H), 4.46 (d, J= 9.2 Hz, 1H), 4.25-4.18 (m, 1H), 3.64 (s, 3H), 3.27-3.34 (m, 1H), 2.88-2.77 (m, 1H), 2.66 (t, J = 7.2 Hz, 2H), 2.42-2.30 (m, 5H), 2.22-2.06 (m, 2H), 1.89-1.74 (m, 5H), 1.62 (d, J= 6.6 Hz, 3H), 1.15 (d, J= 6.7 Hz, 3H), 1.05 (s, 9H). ESI-MS m/z: Calcd. for C68H10oN6Oi4S2: 1288.67. Found: 1289.4(M+H)+.
  • 61
  • [ 14871-92-2 ]
  • sodium perchlorate [ No CAS ]
  • [ 7211-54-3 ]
  • C26H32N6Pd2S2(2+)*2H(1+)*4ClO4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% To a yellow suspension containing 0.20 g (0.60 mmol) of [Pd(bpy)Cl2] in water (20 mL)was added 0.08 g (0.60 mmol) of HaptHCl. After the mixture was stirred at 50 C for 7 h, theresulting yellow solution was filtered. To the yellow filtrate was added an aqueous solution ofNaClO4 (2 M, 10 mL), followed by standing at room temperature for 1 d. The resulting yellowcrystals of [1](ClO4)4 suitable for X-ray analysis were collected by filtration. Yield: 0.32 g (87%).
  • 62
  • [ 7631-99-4 ]
  • [ 14871-92-2 ]
  • [ 7211-54-3 ]
  • C16H22N4Pd2S2(2+)*2H(1+)*2NO3(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% To a yellow suspension containing 0.10 g (0.31 mmol) of [Pd(bpy)Cl2] in water (10 mL) wereadded a solution containing 0.04 g (0.32 mmol) of HaptHCl in water (10 mL) and an aqueoussolution of NaOH (0.25 M, 2.5 mL). When the mixture was stirred at 50 C for 3 h, the suspensionturned to a yellow solution. After filtration, a saturated aqueous solution of NaNO3 (5 mL) wasadded to the yellow filtrate. The mixture was stood at room temperature for 2 d, and the resultingyellow crystals of [2](NO3)2 was collected by filtration. Yield: 0.03 g (36%).
  • 63
  • [ 7631-99-4 ]
  • [ 14871-92-2 ]
  • [ 7211-54-3 ]
  • C23H23N5Pd2S(2+)*2NO3(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% To a yellow suspension containing 0.30 g (0.90 mmol) of [Pd(bpy)Cl2] in water (20 mL) wereadded a solution containing 0.06 g (0.46 mmol) of HaptHCl in water (10 mL) and an aqueoussolution of NaOH (0.3 M, 10 mL). When the mixture was stirred at 50 C for 3 h, the suspensionturned to a yellow solution. After filtration, a saturated aqueous solution of NaNO3 (10 mL) wasadded to the yellow filtrate, followed by storing in a refrigerator for 1 week. The resulting yellowcrystals of [3](NO3)2 suitable for X-ray analysis were collected by filtration. Yield: 0.19 g (55%).
  • 64
  • 2-chloro-4-[((5,6-dihydrothiazolo[5,4,3-ij]quinolin-2(4H)-ylidene)methyl)-1-phenyl]quinolinium chloride [ No CAS ]
  • [ 7211-54-3 ]
  • C29H28N3S2(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere; Example 28 Preparation of Compound 64 (0257) (0258) A mixture of 2-chloro-4-((5,6-dihydrothiazolo[5,4,3-ij]quinolin-2(4H)-ylidene)methyl)-1-phenyl]quinolinium chloride (0.1 g, 0.21 mmol), <strong>[7211-54-3]3-amino-1-propanethiol hydrochloride</strong> (25 mg, 0.27 mmol) and diisopropylethylamine (47 uL, 0.27 mmol) in CH2Cl2 (10 mL) under N2 was stirred at room temperature overnight. The mixture was concentrated to 5 mL and the orange precipitate (60 mg) was collected by suction filtration and dried to a constant weight.
  • 65
  • [ 5554-48-3 ]
  • [ 125829-10-9 ]
  • [ 7211-54-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; for 504h;Reflux; A suspension of tetrahydro-l,3-thiazine-2-thione (7 g, 53 mol) in cone. HCl (45 mL) was heated to reflux for 3 weeks and the reaction progress was monitored by XH NMR. Cone. HCl was evaporated under reduced pressure the using KOH trap for quenching the HCl vapors until an oil remained, a white precipitate of aptHHCl was obtained by the addition of ethanol/ether. Yield 5.12 g, 76 %. minor product 43 (disulfide) : lH NMR (D20, 400 MHz) delta 3.17 - 3.04 (m, 2 H), 3.00 (t, J = 7.0 Hz, 2 H), 2.15 (p, J = 7.4 Hz, 2 H); 1 C NMR (D20, 100 MHz) delta 37.8, 33.3, 25.5; major product (42): XH NMR (D20, 400 MHz) delta 3.17 - 3.04 (m, 2 H), 2.79 (t, J =7.2 Hz, 2 H), 2.08 (p, J = 7.3 Hz, 2 H); 1 C NMR (D20, 100 MHz) delta 37.9, 33.5, 25.7
  • 66
  • 2-chlorotrityl chloride polystyrene resin [ No CAS ]
  • [ 7211-54-3 ]
  • C22H21ClNPolS [ No CAS ]
  • 67
  • rhodium(III) chloride trihydrate [ No CAS ]
  • [ 7211-54-3 ]
  • fac-[Rh(3-aminopropanethiolate)3] [ No CAS ]
  • 68
  • [ 2127-03-9 ]
  • [ 7211-54-3 ]
  • 3-(2-pyridyldithio)propylamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.4% In methanol; at 20℃; for 48h; <strong>[7211-54-3]3-Mercaptopropylamine hydrochloride</strong> (1.0 g, 7.87 mmol) and 2,2'-dithiodipyridine (Py-SS-Py, 5.2 g, 23.6 mmol) were added to 30 mL of methanol, and the reaction was stirred at room temperature for 48 hours.The methanol was evaporated under reduced pressure, purified over silica gel, and concentrated.Drying under vacuum gave 1.4 g of a pale yellow solid product with a structure of i, yield 75.4%.
74.4% In methanol; at 20℃; for 48h; Mercaptopropylamine hydrochloride (1.0 g, 7.9 mmol)And 2,2'-dithiodipyridine (Py-SS-Py, 2.3 g, 9.4 mmol) was added to 60 mL of methanol.The reaction was stirred at room temperature for 48 hours.The reaction solution was concentrated under reduced pressure.The target product was precipitated with diethyl ether, suction filtered,Vacuum drying as shown in equation e1.39g of light yellow oily liquid product,The yield was 74.4%.
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