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CAS No. : | 14294-10-1 | MDL No. : | MFCD00178434 |
Formula : | C5H10N2OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GSLBUBZXFUYMSW-UHFFFAOYSA-N |
M.W : | 146.21 | Pubchem ID : | 2393544 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.43 |
TPSA : | 70.58 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.63 cm/s |
Log Po/w (iLOGP) : | 1.41 |
Log Po/w (XLOGP3) : | -0.62 |
Log Po/w (WLOGP) : | -0.82 |
Log Po/w (MLOGP) : | -0.78 |
Log Po/w (SILICOS-IT) : | 1.01 |
Consensus Log Po/w : | 0.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.29 |
Solubility : | 75.0 mg/ml ; 0.513 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.39 |
Solubility : | 59.6 mg/ml ; 0.407 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.16 |
Solubility : | 213.0 mg/ml ; 1.46 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.86 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P270-P264-P301+P310+P330-P405 | UN#: | 2811 |
Hazard Statements: | H301 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With hydrogen sulfide; triethylamine In pyridine | |
With hydrogen sulfide; ammonia | ||
Stage #1: N-cyanomorpholine With hydrogenchloride In tetrahydrofuran; diethyl ether at 0℃; for 2h; Stage #2: With LiAlHSH In tetrahydrofuran; diethyl ether at 0℃; for 3h; |
With hydrogen sulfide; ammonia In ethanol at 0℃; for 1.08333h; | 2.55 3-[4-(4-Methyl-2-morpholin-4-yl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenol [55] 3-[4-(4-Methyl-2-morpholin-4-yl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenol [55]. A solution OF MORPHOLINE-4-CARBONITRILE (10 g, 89.19 mmol) in EtOH (65 mL) was cooled on an ice bath. Anhydrous NH3 was bubbled through the solution for 5 min, followed by hydrogen sulfide. Soon after the introduction of H2S a white precipitate was observed. After the addition of both gases for 45 min NH3 addition was stopped and H2S continued for a further 15 minutes. The resulting precipitate was collected, washed with cold water, MEOH and dried under high vacuum to afford morpholine-4-carbothioic acid amide (12.83 g).. Mp. 173-174 °C. IH-NMR (DMSO-D6) D : 3.54 (t, 4H, J= 4.9Hz, CH2), 3.70 (M, 4H, CH2), 7.46 (brs, 2H, NH2). This was converted first to 1- (4-METHYL-2-MORPHOLIN-4-YL- thiazol-5-yl) -ethanone with 3-bromo-pentane-2,4-dione, then with dimethoxymethyl- dimethyl-amine to 3-DIMETHYLAMINO-1- (4-METHYL-2-MORPHOLIN-4-YL-THIAZOL-5-YL)- propenone in the usual manner. The latter enaminone was condensed with N- (3-HYDROXY- phenyl) -guanidine nitrate to afford the title compound as a. pale solid. Mp. 227-229 C. TH- NMR (DMSO-D6) No.: 2.49 (s, 3H, CH3), 3.46 (t, 4H, J= 4.4Hz, CH2), 3.71 (t, 4H, J= 4.4Hz, pyrimidinyl-H), 6.34 (d, 1H, J= 8.8Hz, Ph-H), 6.91 (d, 1H, J= 5.4Hz, pyrimidinyl- H), 7.03 (t, 1H, J = 7.8Hz, Ph-H), 7.20-7. 22 (M, 2H, Ph-H), 8.34 (d, 1H, J = 5.4Hz, pyrimidinyl-H), 9.17 (s, 1H, OH/NH), 9.32 (s, 1H, NH/OH). MS (ES¢) M/Z 370.10 [M+H] + (CI8HI9NS02S requires 369.44). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogenchloride In methanol for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With perchloric acid; boron trifluoride diethyl etherate In acetic acid for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With perchloric acid; boron trifluoride diethyl etherate In acetic acid for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol; acetic acid for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With perchloric acid; boron trifluoride diethyl etherate In acetic acid at 80℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In methanol; acetic acid for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With perchloric acid; boron trifluoride diethyl etherate In acetic acid for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With perchloric acid; boron trifluoride diethyl etherate In acetic acid for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With perchloric acid In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With perchloric acid; boron trifluoride diethyl etherate In acetic acid for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With perchloric acid In acetic acid at 80℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With perchloric acid; trichlorophosphate In acetic acid for 4h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With perchloric acid; trichlorophosphate In acetic acid for 4h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With perchloric acid In acetic acid for 0.166667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With perchloric acid In acetic acid for 0.166667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With perchloric acid In acetic acid for 0.166667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With perchloric acid In acetic acid for 0.166667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With perchloric acid In acetic acid for 0.166667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With perchloric acid In acetic acid for 0.166667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In acetone 1) 5 h, reflux, 2) RT, 12 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | at 120℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With perchloric acid; boron trifluoride diethyl etherate In acetic acid for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(II) bis(trifluoromethanesulfonate); potassium carbonate In acetonitrile at 70℃; for 0.25h; chemoselective reaction; | |
51% | With diethoxydisulfane In acetonitrile for 11h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In ethanol for 0.666667h; Heating; | |
In N,N-dimethyl acetamide at 20℃; for 0.5h; | ||
In ISOPROPYLAMIDE at 25℃; for 0.5h; | 31 EXAMPLE 31. 4- 4-(4-BROMOPHENYL)THIAZOL-2-YL)MORPHOLINE (XJBOl-016)[0138] Morpholine-4-carbothioamide (105 mg, 0.720 mmol) was added to a solution of 2-bromo-l-(4-bromophenyl)ethanone (100 mg, 0.360 mmol) in DMA (2.00 mL). The reaction mixture was stirred at room temperature for 0.5 h and poured into water. The precipitation was collected by filtration and dried overnight to afford a white solid: 1H NMR (400 MHz, DMSO-d6) δ 7.83-7.80 (m, 2 H), 7.59-7.56 (m, 2 H), 7.39 (s, 1 H), 3.73 (t, 7=5.0 Hz, 4 H), 3.44 (dd, 7=4.0, 5.2 Hz, 4 H); LCMS RT = 6.561 min, m/z 325.0 [M+H+] ; HRMS (ESI) m/z calcd for Ci3Hi479BrN2OS [M+H+] 325.0010. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In ethanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | In acetonitrile at -20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia 1.) THF, a) RT, 2 h, b) 55 deg C, 1 h, 2.) THF, 15 h; Yield given; Multistep reaction; | ||
Stage #1: morpholine; 1,1'-Thiocarbonyldiimidazole In tetrahydrofuran at 20 - 55℃; for 2h; Stage #2: With ammonia In tetrahydrofuran; ethanol at 20 - 55℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane at 120℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium sulfate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium hydroxide In tetrahydrofuran Yield given; | ||
With ammonia In tetrahydrofuran; methanol at 20℃; for 72h; | 13 INTERMEDIATE 13Morpholine-4-carbothioamide To a stirred solution of 1 , 1 '-thiocarbonyldiimidazole (10.0 g, 56.1 mmol) in THF(150 mL) was added morpholine (4.24 g, 4.2 mL, 48.7 mmol). The reaction was stirred for 72 h at r.t. and then concentrated in vacuo to 30 mL. Ammonia (60 mL, 2.0M in MeOH) was added to the reaction mixture, which was then stirred at r.t. in a sealed flask overnight. The reaction mixture was filtered and the solid washed with Et2O to give the title compound (2.0 g, 28%) as a white solid. δH (DMSO-d6) 7.46 (2H, bs), 3.80-3.60 (4H, m), 3.60-3.50 (4H, m). | |
515 mg | With ammonia In tetrahydrofuran; methanol at 20 - 50℃; for 23h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With sodium hydrogencarbonate In acetonitrile for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogen sulfide In tetrahydrofuran at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In ethanol at 120℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; for 3.5h;Heating / reflux; | 4- (2-bromoacetyl) benzoic acid (1.23 mmol) and 1-morpholinethiocarboxamide (1.23 mmol, J. Med. Chem 1998, 41, 5037-5054) were mixed in THF (10 mL), then refluxed for 3.5 h. The reaction mixture was then allowed to reach room temperature and the obtained precipitate was collected by filtration and washed with 4 portions of diethyl ether. The crude product was crystallized from hot 1: 1 EtOH-EtOAc to give a first harvest of colorless needles (0.16 g, 0.55 mmol). 1H NMR (DMSO-d6, 400 MHz) 8 7.94 (4H, m), 7.49 (1 H, s), 3.72 (4H, m), 3. 44 (4H, m). | |
In tetrahydrofuran; for 3.5h;Heating / reflux; | <strong>[20099-90-5]4-(2-bromoacetyl)benzoic acid</strong> (1.23 mmol) and 1-morpholinethiocarboxamide (1.23 mmol, J. Med. Chem 1998, 41, 5037-5054) were mixed in THF (10 ml_), then refluxed for 3.5 h. The reaction mixture was then allowed to reach room temperature and the obtained precipitate was collected by filtration and washed with 4 portions of diethyl ether. The crude product was crystallized from hot 1 :1 EtOH-EtOAc to give a first harvest of colorless needles (0.16 g, 0.55 mmol). 1 H NMR (DMSO-d6, 400 MHz) delta 7.94 (4H, m), 7.49 (1 H, s), 3.72 (4H, m), 3.44 (4H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 85℃; for 1h; | 1 EXAMPLE 1; 6,6-Dimethyl-2-(morpholin-4-yl)-6,7-dihvdro[l,31thiazolo[5,4-clpyridin-4(5H)-one; To a stirred suspension of Intermediate 3 (0.10 g, 0.71 mmol) in TηF (3 mL) was added Br2 (0.12 g, 0.04 mL, 0.74 mmol) dropwise at 00C. The reaction mixture was allowed to warm to r.t. and Intermediate 7 (0.16 g, 0.71 mmol), DIPEA (0.19 g, 0.25 mL, 1.42 mmol) and TηF (3 mL) were added. After stirring at 85°C for 1 h, the reaction mixture was poured into water (5 mL) and the aqueous layer was extracted with EtOAc (2 x 5 mL). The combined organic layers were washed with water (3 x 7 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 1 :1 EtOAc/hexanes) to give the title compound (0.07 g, 35%) as a yellow solid. δη (DMSO-d6) 7.30 (IH, br. s), 3.70 (4H, t, J 4.9 Hz), 3.47 (4H, t, J 4.9 Hz), 2.70 (2H, s), 1.24 (6H, s). LCMS (ES+) 268.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | Stage #1: morpholinothiourea; tert-butyl 3-bromo-2,4-dioxooctahydro-1H-cyclopenta[b]pyridine-1-carboxylate In ethanol at 70℃; for 6h; Stage #2: With water; sodium carbonate In ethanol; ethyl acetate | 4 EXAMPLE 4; 2-(Morpholin-4-yl)-5,5a,6.7.8.8a-hexahvdro-4H-cvclopenta[Z?irL31thiazolor4.5- flηpyridin-4-one ; To a stirred solution of Intermediate 14 (0.26 g, 0.79 mmol) in EtOH (10 mL) was added Intermediate 7 (0.12 g, 0.83 mmol) and the reaction mixture was stirred at 7O0C for 6 h. The reaction mixture was then partitioned between EtOAc (15 mL) and aqueous sat. NaHCO3 solution (15 mL) and the organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, EtOAc), followed by preparative HPLC, gave the title compound (0.03 g, 14%) as an off-white solid. 5H (CD3OD) 4.17-4.11 (IH, m), 3.82-3.79 (4H, m), 3.58-3.55 (4H, m), 3.27-3.19 (IH, m), 2.25-2.19 (IH, m), 2.17-2.02 (IH, m), 2.00-1.64 (4H, m). Exchangeable proton not observed. LCMS (ES+) 280.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / Heating 2: Et3N; HATU / dimethylformamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: MgSO4 / acetone / Heating 2: LiAlH4 / tetrahydrofuran; toluene / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dioxane / 16 h / 120 °C 2: LiAlH4 / tetrahydrofuran / 45 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dioxane / 16 h / 120 °C 2: LiAlH4 / tetrahydrofuran / 45 h / Ambient temperature 3: Ph3P, DEAD / tetrahydrofuran / Ambient temperature 4: aq. LiOH / tetrahydrofuran / 2.5 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dioxane / 16 h / 120 °C 2: LiAlH4 / tetrahydrofuran / 45 h / Ambient temperature 3: Ph3P, DEAD / tetrahydrofuran / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 120℃; for 0.233333h; Microwave; | 192 To N- [3- (6 (R, S) -bromo-5-oxo-6, 7,8, 9-tetrahydro-5H-benzocyclohepten-2- YL)-2-OXO-OXAZOLIDIN-5 (S) -ylmethyl]-acetamide (251.2 mg, 0.636mmol) dissolved in warm ethanol (1 ML) was added morpholine-4-carbothioic acid amide (92.9 mg, 0.636 mmol). The resulting mixture was heated in microwave reactor at 120 C for 14 minutes. The solid was filtered out, washed with ethyl acetate (2 mL) and dried to give the title compound. Isolated yield: 170.8 mg. MS- APCI (m/z+): 399,443 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux; | |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 85℃; for 2h; | 1 EXAMPLE 1 2-(Moφholin-4-yl)-4H-spiro[l,3-benzothiazole-5J'-cyclopentan1-7('6H)-oneTo a stirred solution of spiro[4,5]decane-7,9-dione (1.03 g, 6.2 mmol) in AcOH (10 mL) was added bromine (0.99 g, 0.32 rnL, 6.2 mmol) dropwise. The reaction mixture was stirred for 2 h and then the product was isolated by filtration. The precipitate was washed twice with Et2O (100 mL) and then dried in vacuo. The crude product (0.44 g) was dissolved in TΗF (50 mL). Intermediate 13 (0.262 g, 1.8 mmol) and N, N- diisopropylethylamine (0.23 g, 0.31 mL, 1.8 mmol) were added. The reaction mixture was heated to 85°C for 2 h and then poured into NaHCO3 solution (150 mL) and extracted with EtOAc (150 mL). The organic fraction was dried over MgSO4 and concentrated in vacuo. The crude product was subjected to column chromatography (SiO2, EtOAc) to yield the title compound (0.03 g, 2%, 2 steps) as a white solid, δϖ (DMSO-d6) 3.73-3.68 (4H, m), 3.59-3.48 (4H, m), 2.74 (2H, s), 2.42 (2H, s), 1.68-1.57 (4H, m), 1.57-1.38 (4H, m). LCMS (ES+) 293.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 85℃; | 2; B EXAMPLE 2 (METHOD B)5-Isopropyl-2-(morpholin-4-ylV5,6-dihvdro-l,3-benzothiazol-7(4H)-oneTo a stirred solution of Intermediate 3 (1 g, 4.2 mmol) in TΗF (50 mL) was added Intermediate 13 (0.62 g, 4.2 mmol) and Λζ,N-diisopropylethylamine (0 54 g, 0.73 mL, 4.2 mmol). The reaction mixture was heated to 85°C overnight and then poured onto NaHCO3 solution (150 mL) and extracted with EtOAc (150 mL) twice. The organic fraction was dried over MgSO4 and concentrated in vacuo. The solid was chromatographed (SiO2, hexane-DCM) and then triturated with MeCN to yield the title compound (0.22 g, 19%) as a white solid. δH (DMSO-d6) 3.69 (4H, d, J5.2 Hz), 3.55 (4H, d, J5.2 Hz), 2.80 (IH, dd, J 16.0 and 3.8 Hz), 2.55-2.23 (3H, m), 2.08-1.90 (IH, m), 1.69-1.58 (IH, m), 0.91 (6H, d, J6.7 Hz). LCMS (ES+) 281.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol | 24 4-Morpholinecarboximidic acid, 2,2'-(9,10-anthrylenedimethylidyne)hydrazide dihydroiodide EXAMPLE 24 4-Morpholinecarboximidic acid, 2,2'-(9,10-anthrylenedimethylidyne)hydrazide dihydroiodide A solution of 4.65 g. of 4-morpholinethiocarboxamide [W. G. Finnegan, et al., J. Org. Chem. 18, 779 (1952)] and 4.54 g. of iodomethane in 50 ml. of ethanol is allowed to stand 48 hours at room temperature, then diluted with 250 ml. of ether to give a colorless crystalline precipitate of methyl 4-morpholinethiocarboximidate hydroiodide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | In ethanol for 1.5h; Reflux; | |
35% | In ethanol at 80℃; for 16h; | 2a Preparation of 4-(4-(chloromethyl)thiazol-2-yl)morpholine 1,3-Dichloroacetone (3.34 g, 0.020 mol, 1 equiv) was added to a stirred solution of morpholine-4-carbothioamide (13) (3.0 g, 0.020 mol, 1 equiv) in EtOH (30 mL) at ambient temperature. The reaction mixture was stirred at 80 °C for 16 h, and then cooled to ambient temperature. The resultant mixture was concentrated under vacuum. The residue was basified with 10% NaHC03 aqueous solution and extracted with DCM (2X100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over Na2S04, filtered and concentrated under vacuum. The crude product was purified by silica gel column chromatography (10% ethyl acetate-hexanes) to provide compound 14 as a colorless liquid (1.55 g, 35%). LC-MS (ESI+): m/z 218.9 (M+H)+ |
In ethanol for 1h; Heating / reflux; | 13.1 11.51 g (78.76 mmol) of 4-moφholinecarbothioamide and 10.00 g (78.76 mmol) of dichloroacetone in 100 ml of ethanol are heated under reflux for one hour. The colourless solid which precipitates from the pink solution is, after cooling, filtered off with suction and washed twice with ethanol. This gives 12.96 g (75% of theory) of product.MS (ESIpos): m/z = 219 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With pyridine In toluene Ar-atmosphere; stirring (90°C, 5 h); filtering, washing (toluene), washing (H2O), drying (Na2SO4), evapn., pptn. on n-hexane addn., recrystn. (toluene); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In ethanol at 80℃; for 3h; | 43.I A mixture of ethylmalonylchloride (4.76 mL, 35 mmol) and morpholine-4-carbothioic acid amide (5.0 g, 34.2 mmol) in ethanol (40 mL) was heated to 80 0C for 3 hours. The mixture was cooled, ethanol evaporated, and diluted with saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layers were dried over magnesium sulfate and the reaction mixture purified by chromatography (silica gel; ethylacetate/hexane, 1 :1 ) to provide ethyl (2-morpholin-4-yl-1 ,3-thiazol-4-yl)acetate (9 g, quantitative) |
100% | Stage #1: morpholinothiourea; ethyl (2-chloroaceto)acetate In ethanol at 80℃; for 3h; Stage #2: With water; sodium hydrogencarbonate | 15.I Part I: Preparation of ethyl (2-morpholin-4-yl-1 ,3-thiazol-4-yl)acetateA mixture of ethylmalonylchloride (4.76 mL, 35 mmol) and morpholine-4-carbothioic acid amide (5.0 g, 34.2 mmol) in ethanol (40 mL) was heated to 80 0C for 3 hours.The mixture was cooled, ethanol evaporated, and diluted with saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layers were dried over magnesium sulfate and the reaction mixture purified by chromatography (silica gel; ethylacetate/hexane, 1 :1 ) to provide ethyl (2-morpholin-4-yl-1 ,3-thiazol-4-yl)acetate (9 g, quantitative) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 1.5h; | 2 To a stirred solution of Intermediate 1 (0.16 g, 0.71 mmol) in TηF (3 mL) was added morpholine-4-carbothioamide (WO 2006/114606) (0.11 g, 0.71 mmol) and DIPEA (0.25 mL, 1.42 mmol). The reaction mixture was heated to 600C for 1.5 h, then cooled to r.t. and partitioned between EtOAc (10 mL) and water (10 mL). The aqueous fraction was separated and extracted with EtOAc (3 x 5 mL). The combined organic fractions were washed with water (3 x 10 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 1 : 1 EtOAc/hexanes) gave the title compound (0.07 g, 35%) as a yellow solid. δη (DMSO-d6) 7.30 (IH, br. s), 3.72-3.65 (4H, m), 3.51-3.45 (4H, m), 2.70 (2H, s), 1.24 (6H, s). LCMS (ES+) 268.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.5% | Stage #1: (3-(2-(2-chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)allylcarbamate With N-Bromosuccinimide In ISOPROPYLAMIDE at 20℃; for 1h; Inert atmosphere; Stage #2: morpholinothiourea In ISOPROPYLAMIDE at 0 - 20℃; for 2h; Inert atmosphere; | To a solution of 2-propen-1 -yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2- fluorophenyl}carbamate (20 g, 57 mmol) in DMA (300 ml_) was added NBS (10.2 g, 57 mmol). The reaction mixture was stirred at room temperature for 1 h. Then 4-morpholinecarbothioamide (9.2 g, 63 mmol) was added at 0 °C. The mixture was stirred at room temperature for 2 h. The mixture was poured into water and extracted with EtOAc (1 L x 3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (DCM etroleum ether 2:1 ) to afford the title compound. 20 g (83.5% yield) 1 H NMR (400 MHz, CDCI3) δ ppm 8.20- 8.27 (m, 1 H), 8.19 (d, J=5.5 Hz, 1 H), 7.20-7.26 (m, 1 H), 7.08-7.12 (m, 1 H), 6.92-6.98 (br, 1 H), 6.62 (d, J=5.5 Hz, 1 H), 5.90-6.03 (m, 1 H), 5.25-5.41 (m, 2H), 5.65-5.70 (m, 2H), 3.57-3.63 (m, 4H), 3.77-3.86 (m, 4H). m/z (ES+): 476 [M+H]+ |
83.5% | Stage #1: (3-(2-(2-chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)allylcarbamate With N-Bromosuccinimide In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: morpholinothiourea In N,N-dimethyl acetamide at 0 - 20℃; | 26 Intermediate 26: 2-Propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate; To a solution of 2-propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate (20 g, 57 mmol) (Intermediate 20) in DMA (300 mL), NBS (10.2 g, 57 mmol) was added. The reaction mixture was stirred at rt for 1 h. Then morpholine-4-carbothioamide (9.2 g, 63 mmol) was added at 0° C. The mixture was stirred at rt for 2 h. The mixture was poured into water and extracted with EtOAc (1 L×3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (DCM:petroleum ether 2:1) to afford the title compound (20 g, 83.5% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.20-8.27 (m, 1H), 8.19 (d, J=5.5 Hz, 1H), 7.20-7.26 (m, 1H), 7.08-7.12 (m, 1H), 6.92-6.98 (br, 1H), 6.62 (d, J=5.5 Hz, 1H), 5.90-6.03 (m, 1H), 5.25-5.41 (m, 2H), 5.65-5.70 (m, 2H), 3.57-3.63 (m, 4H), 3.77-3.86 (m, 4H). m/z (ES+): 476 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.8% | Stage #1: 2-propen-1-yl [3-[(2-chloro-4-pyrimidinyl)acetyl]-2-(methyloxy)phenyl]carbamate With N-Bromosuccinimide In dichloromethane at 20℃; for 0.5h; Stage #2: morpholinothiourea In dimethyl sulfoxide at 20℃; for 1h; | 47.A Example 47; 2,6-Difluoro-N-{2-(methyloxy)-3-[5-{2-[(2-methylpropyl)amino]-4-pyrimidinyl}-2-(4-morpholinyl)-1,3-thiazol-4-yl]phenyl}benzenesulfonamide; Step A: 2-Propen-1-yl [3-[5-(2-chloro-4-pyrimidinyl)-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2-(methyloxy)phenyl]carbamate; To a solution of 2-propen-1-yl [3-[(2-chloro-4-pyrimidinyl)acetyl]-2-(methyloxy)phenyl]carbamate (30 g, 82.9 mmol) in DCM (300 mL), NBS (14.8 g, 82.9 mmol) was added and the solution was allowed to stir at rt for 30 min. The reaction mixture was then concentrated on the rotovap and the resulting oil was diluted with DMSO (240 mL) and 4-morpholinecarbothioamide (14.8 g 101 mmol) was added at once. The reaction was complete after stirring 1 h at rt. The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product which was purified by column chromatography on silica gel (DCM:petroleum ether 2:1) to afford the product of Step A (40 g, 98.8% yield) which was used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.8% | In ethanol; for 1h;Reflux; | Step 1 : 2-Bromo-l-pyridin-4-yl-ethanone hydrobromide (1.0 g, 3.55 mmol) and morpholine-4-carbothioamide (0.520 g, 3.55 mmol) were dissolved in EtOH (20 mL) and the mixture was refiuxed for lhr. After cooling, the yellow solids were collected by filtration, 74.8% yield. [M+H]+ m/z 248. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / ISOPROPYLAMIDE / 1 h / 20 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl acetamide / 1 h / 20 °C 1.2: 0 - 20 °C 2.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / ISOPROPYLAMIDE / 1 h / 20 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 3.1: pyridine / 72 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Stage #1: N-{3-[(2-chloro-4-pyrimidinyl)acetyl]-2,4-difluorophenyl}-1-propanesulfonamide With N-Bromosuccinimide In ISOPROPYLAMIDE at 0℃; for 0.5h; Inert atmosphere; Stage #2: morpholinothiourea In ISOPROPYLAMIDE at 60℃; for 4h; Inert atmosphere; | 36.3 To a solution of A/-{3-[(2-chloro-4-pyrimidinyl)acetyl]-2,4-difluorophenyl}-1 - propanesulfonamide (9.5 g, 24.4 mmol) in DMA (100 mL) was added NBS(44.34 g, 24.4 mmol) at 0 °C. After 30 min, 4-morpholinecarbothioamide (4.28 g, 29.3 mmol) was added to the reaction mixture and heated at 60 °C for 4h.The reaction mixture was poured into water and extracted with EtOAc (2x).The combined organic layer were washed with water, brine, dried, filtered, and concentrated. The residue was chromatographed on a silica gel column and eluted with (CH2CI2: EtOAc, 20:1 ) to obtain A/-{3-[5-(2-chloro-4- pyrimidinyl)-2-(4-morpholinyl)-1 ,3-thiazol-4-yl]-2,4-difluorophenyl}-1 - propanesulfonamide (4.8 g, 39%). MS: 516 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With toluene-4-sulfonic acid In ethanol; water at 90℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogenchloride In water at 75 - 80℃; | Synthesis of morpholine-4-carbothioamide 2 To the stirred solution of ammonium thiocyanate (0.263 moles, 1 eq) and acetone (400 ml) at 0°C benzoyl chloride (0.263 moles, 1 eq) was added dropwise. The reaction mass was heated to reflux (60 degrees) for 30 mins and then the reaction mass was cooled to 40°C, then solution of morpholine (0.25 moles, 0.95 eq) in acetone was added dropwise such that the reflux temperature of reaction mass is maintained. After complete addition the reaction mass was heated to reflux for 1 hour and then RM was cracked over ice with thorough stirring. Solids were formed which were filtered and thorough washing with water was given to remove benzoyl chloride, ammonium thiocyanate and morpholine. Solids of N-(morpholine-4-carbonothioyl)benzamide were dried first under vacuum and then in oven. Yield: 22.33 g (34%), MP: 155°C. N-(morpholine-4-carbonothioyl)benzamide (22.33 g, 0.089 mol) and conc HCl (130 ml) was added to round bottom flask equipped with overhead stirrer. The reaction mass was heated to 75-80°C and stirred overnight. White colored solids was seen. Next day reaction was stopped and cooled to room temperature and then further cooled to 10°C and then neutralized with ammonia solution which gave formation of crystalline solids. Solids were then taken in saturated NaHCO3 solution and then stirred for 30 mins to remove benzoic acid. Solids of morpholine-4-carbothioamide were filtered and then taken into 20% ethyl acetate in hexane to remove non polar impurities. Yield: 12.4 g (92%), MP: 175°C. |
79.6% | With hydrogenchloride at 75℃; for 12h; | 2 2.4.2 Synthesis of morpholine-4-carbothioamide (2) The solution of compound 1 (20 g, 0.08 mol) in 120 mL conc. HCl was stirred for 12 h at 75 °C using overhead stirrer. Then the reaction mixture was cooled to RT and to this was added few ice cubes. The resulting mixture was neutralized using liquid ammonia. The crude pale yellow solid obtained after filtration under vacuum was washed with ice cold water followed by dilute sodium bicarbonate solution furnished the desired product (2) as an off white solid. (9.3 g, 79.6%); Mp-175 to °C-176 °C (Literature Mp-176 °C to 177 °C) |
78% | With hydrogenchloride at 75 - 80℃; for 4h; | 2.2.3 Synthesis of morpholine-4-carbothioamide (4) N-(Morpholin-4-yl-carbonothioyl) benzamide (3) (10.50g 41.9mmol)was charged in conc. HCl (20mL) and the mixture is stirred at 75-80°C for 4h, completion of the reaction was monitored by TLC. The reaction mixture then brought to room temperature then neutralized with liq. ammonia, extracted with 1,2-dichloroethane dried over Na2SO4 and solvent removed under reduced pressure. The resulting crude mass was recrystallized from ethanol as a solvent [20b].Yield: 78%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In ethanol Reflux; | 2.2.4 Synthesis of 2-(morpholin-4-yl)-1,3-thiazol-4(5H)-one hydrochloride (5 Morpholine-4-carbothioamide (4) (5g, 34.2mmol) and ethyl chloroacetate (4mL, 37.6mmol) were heated to reflux for 3h in ethanol, completion of the reaction was monitored by TLC. Diethyl ether was added to the resulting reaction mass slowly and precipitated product filtered off dried [19].Yield: 61% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In chloroform at 20℃; for 1h; | 94AAA Morpholine-4-carbothioamide To a solution of morpholine (199 g, 2280 mmol) in CHC13 (1 L) was added isothiocyanatotrimethylsilane (150 g, 1140 mmol) dropwise. A white precipitate formed almost immediately, and the reaction was stirred for 1 h at RT. The reaction was then filtered and the resulting solid was washed with additional CHC13 and dried in vacuo to give the title thiourea as a white solid. (137 g, 937 mmol, 82%). 1H NMR (400MHz, DMSO-d6) δ 3.81 - 3.71 (m, 2H), 3.17 - 3.08 (m, 2H). |
In chloroform at 20℃; for 1h; | 88 At room temperature, To compound 88-3 (3.32 mL, 38.1 mmol) Chloroform (20mL) (Trimethylsilyl)isothiocyanate(2.68 mL, 19.1 mmol) was added dropwise to the solution, Immediately produced a large amount of white solid, Continue stirring for 1 hour. After the reaction was completed, it was filtered, and the filter cake was washed with chloroform (2 mL x 3). The filter cake was dried under vacuum overnight to give compound 88-4 (white solid, 2.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In methanol for 1h; Reflux; | 94A Methyl 5-methyl-2-morpholinothiazole-4-carboxylate To a solution of morpholine-4-carbothioamide (Example 94 AAA, 175 g, 1200 mmol) in methanol (500 mL) was charged methyl 3-bromo-2-oxobutanoate (Example 94AA, 233 g, 1200 mmol). The reaction was then heated to reflux for 1 hour, cooled to RT, and filtered. The filtrate was concentrated and the crude product was purified on by silica gel chromatography. The title thiazole (206g, 850 mmol, 71%) was isolated as a yellow oil. (See the procedure set forth above for analytical data). |
1.7 g | In methanol for 1h; Reflux; | 88 Weigh compound 88-2 (3.33 g, 17.1 mmol) And compound 88-4 (2.5 g, 17.1 mmol) were dissolved in methanol (30 mL), The temperature was raised to reflux and heated for 1 hour. After the reaction is complete, The solution was evaporated under reduced pressure, The residue was purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 4: 1), Compound 88-5 (yellow transparent oil, 1.7 g) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: 4-methyl-morpholine; 1,1'-Thiocarbonyldiimidazole In tetrahydrofuran at 55℃; for 3h; Stage #2: With ammonia In tetrahydrofuran at 55℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: morpholinothiourea; 2-bromo-1-(3-fluoro-2-methanesulfonylphenyl)ethanone In ethanol for 1h; Heating; Stage #2: With sodium hydrogencarbonate at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In ethanol at 0℃; for 4h; Reflux; | 2,3-Difluoro-6-(2-morpholinothiazol-4-yl)phenol (ARB-1) 2,3-Difluoro-6-(2-morpholinothiazol-4-yl)phenol (ARB-1) The titled compound can be prepared according to the process described by Huifang Li et al. J. Med. Chem. 2014, 57, 6458-6467. Morpholine-4-carbothioamide (commercially available from, for example, Fluorochem) (0.330 g, 2.26 mmol) was added in small portions to a stirred solution of compound 2-bromo-1-(3,4-difluoro-2-hydroxyphenyl)ethan-1-one (C) (0.568 g, 2.26 mmol) in absolute EtOH (10 mL) at 0° C. When addition was completed, the mixture was refluxed for 4 h. After cooling at rt, the mixture was evaporated to dryness and NaHCO3 saturated solution (20 mL) was added to pH 8. The aqueous phase was extracted with EA (10 mL*3), the reunited organic phases were dried over anhydrous Na2SO4 and concentered under reduced pressure to give a solid which was tritured with DEE and filtered affording the titled compound (0.590 g, 87% yield) as a light-yellow solid. 1H NMR (400 MHz, CDCl3): δ 12.43 (s, 1H), 7.24 (ddd, J=2.3, 5.6, 8.5 Hz, 1H), 6.76 (s, 1H), 6.66 (td, J=7.2, 9.3 Hz, 1H), 4.00-3.84 (m, 4H), 3.63-3.43 (m, 4H); 13C NMR (101 MHz, CDCl3): δ 171.13, 151.23 (dd, J=10.4, 247.9 Hz), 148.09, 147.25-146.05 (m), 140.72 (dd, J=14.2, 244.7 Hz), 119.63 (dd, J=4.5, 8.7 Hz), 115.71, 106.97 (d, J=18.4 Hz), 100.25 (d, J=1.7 Hz), 65.90 (2C), 48.31 (2C). |
In ethanol at 20℃; for 4.16667h; Heating; | ||
With copper(ll) bromide In ethanol for 4h; Reflux; | 1 Scheme 1. Synthesis of ARB-1 moiety: |
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