Structure of 64837-49-6
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
Change View
| Size | Price | VIP Price |
DE Stock US Stock |
Asia Stock Global Stock |
In Stock |
| {[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock Inquiry - | Login - + |
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 7-10 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 7-10 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
| CAS No. : | 64837-49-6 |
| Formula : | C5H5ClN2O2S |
| M.W : | 192.62 |
| SMILES Code : | ClC1=NN=C(S1)C(=O)OCC |
| English Name : | Ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate |
| MDL No. : | MFCD11112114 |
| InChI Key : | YQWCUJDSRXQJRN-UHFFFAOYSA-N |
| Pubchem ID : | 12348753 |
| Num. heavy atoms | 11 |
| Num. arom. heavy atoms | 5 |
| Fraction Csp3 | 0.4 |
| Num. rotatable bonds | 3 |
| Num. H-bond acceptors | 4.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 41.01 |
| TPSA ? Topological Polar Surface Area: Calculated from |
80.32 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.98 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.88 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.37 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.25 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.46 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.59 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-2.36 |
| Solubility | 0.847 mg/ml ; 0.0044 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-3.19 |
| Solubility | 0.125 mg/ml ; 0.000647 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.02 |
| Solubility | 1.83 mg/ml ; 0.00951 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
| BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.14 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.89 |
* 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 |
|---|---|---|
| In acetonitrile; at 0 - 20℃; | Ethyl diazoacetate (1, 10 g, 87.6 mmol) was taken up in acetonitrile (50 mL) and the resultant mixture cooled to 0 C. Thiophosgene (3.4 mL, 43.8 mmo.) was added to the mixture dropwise and the mixture was then stirred at room temperature for 20 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated from the reaction mixture under reduced pressure. The resultant crude product was purified by column chromatography using 10% EtOAc-hexane to afford ethyl 5-chloro-l ,3,4-thiadiazole-2-carboxylate (2, 3, 4 g, 25%). NMR (400 MHz, CDCI3): delta 4.57 (q, 2H), 1.42 (t, 3H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In DMF (N,N-dimethyl-formamide); at 70 - 80℃; for 18.0h; | Synthesis of 5-(7-Chloro-quinolin-4-yloxy)-[1,3,4]thiadiazole-2-carboxylic Acid Ethyl Ester [CHEMMOL-00141] [0176] NaH (0.022 mg, 0.5 mmol) was added in portions to a solution of 7-chloro-4-hydroxyquinoline (0.093 mg, 0.5 mmol) in DMF (6 ml) at room temperature and the mixture stirred at room temperature for 20 min. 2-Chloro-[1,3,4]thiadiazole derivative (0.097 mg, 0.5 mmol) was then added in one portion and the mixture heated at 70-80 C. (oil bath temperature) for 18 h. The reaction mixture was allowed to cool to room temperature and water (15-30 ml) was added. The precipitate was separated by filtration, washed several times with cold water, then with Et2O and dried to afford the product (0.081 mg, 47% yield). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In DMF (N,N-dimethyl-formamide); at 80℃; for 18.0h; | Synthesis of 5-Chloro-[1,3,4]thiadiazole-2-carboxylic Acid (7-chloro-quinolin-4-yl)-amide [CHEMMOL-00146] [0186] NaH (0.023 g, 0.58 mmol) was added in portions to a solution of 4-amino-7-chloro-quinoline (0.1 g, 0.56 mmol) in DMF (6 ml) at room temperature and the mixture was stirred for 20 min. 5-Chloro-[1,3,4]thiadiazole derivative (0.108 g, 0.56 mmol) was then added in one portion and the mixture heated at 80 C. (oil bath temperature) for 18 h. The reaction mixture was allowed to cool to room temperature and water (15 ml) was added. The precipitate was separated by filtration, washed with Et2O and dried to afford the product (0.08 g, 60% yield). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | With sodium borohydrid; In methanol; | Preparation 39 Synthesis of (5-chloro-1,3,4-thiadiazol-2-yl)methanol To a solution of <strong>[64837-49-6]ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate</strong> (0.51 g, 2.60 mmol) in anhydrous methanol (5.00 mL) was added sodium borohydride (0.30 g, 7.99 mmol) at 0 C. The reaction mixture was stirred at ambient temperature for 16 h, diluted with acetic acid (3.00 mL) and extracted with ethyl acetate (2*150 mL). The combined organics was washed with aqueous saturated sodium bicarbonate (3*25.0 mL) and aqueous saturated sodium chloride (2*25.0 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to give the title compound (0.30 g, 75%) as a light yellow semi-solid: 1H NMR (300 MHz, CDCl3) delta 5.04 (s, 2H), 2.80 (br, 1H); MS (ES+) 151.1 (M+1), 153.1 (M+1). |
| 75% | With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 16.0h; | To a a solution of <strong>[64837-49-6]ethyl 5-chloro-1 ,3,4-thiadiazole-2-carboxylate</strong> (0.51 g, 2.60 mmol) in anhydrous methanol (5.00 mL) was added sodium borohydride (0.30 g, 7.99 mmol) at 0 0C. The reaction mixture was stirred at ambient temperature for 16 h, diluted with acetic acid (3.00 mL) and extracted with ethyl acetate (2 x 150 mL). The combined organics was washed with aqueous saturated sodium bicarbonate (3 x 25.0 mL) and aqueous saturated sodium chloride (2 x 25.0 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to give the title compound (0.30 g, 75%) as a light yellow semi-solid: 1H NMR (300 MHz, CDCI3) delta 5.04 (s, 2H), 2.80 (br, 1 H); MS (ES+) 151.1 (M + 1), 153.1 (M + 1). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 25% | With toluene-4-sulfonic acid; In Isopropyl acetate; at 80℃; | Ethyl 5-chloro-l ,3,4-thiadiazole-2 -carboxylate (3, 3 g, 15.7 mmol), 2-methoxy-4-(4-methyl piperazin-l -yl)aniline (4, 3.4 g, 15.7 mmol) and p-TSA (3 g, 15.7 mmol) were taken up in IPA (25 mL) and the resultant mixture was stirred at 80 C overnight. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated from the reaction mixture under reduced pressure, and the resultant residue was basified using aq. NaHC03 solution and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resultant crude product was purified by columnchromatography using 5% MeOH-DCM to afford ethyl 5-((2-methoxy-4-(4-methylpiperazin-l - yl)phenyl)amino)-l ,3,4-thiadiazole-2-carboxylate (5, 1 .5 g, 25%). NMR (400 MHz, CDC13): delta 7.90 (bs, 1 H), 7.43 (d, 1 H), 6.59-6.55 (m, 2H), 4.50 (q, 2H), 3.90 (s, 3H), 3.25-3.22 (m, 4H), 2.65- l .60 (m, 4H), 2.40 (s, 3H), 1.42 (t, 3H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 73% | With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 3.0h; | Step 1. General procedure for preparation of Intermediate 8. 8 A solution of ethyl 5-chloro-l,3,4-thiadiazole-2-carboxylate (60 g, 0.313 mol), K2CO3 (130 g, 0.94 mol) and methyl piperazine in DMF (300 mL) was stirred at 40 C for 3 h. TLC Rf 0.5 (petroleum ether/EtOAc, 10/1) showed the reaction was complete. The reaction mixture was poured into water and extracted with. CH2CI2. The organic layer was washed with water, dried over Na2S04, and concentrated to give Intermediate 8 (58.5 g, 73%) as a yellow solid. 1H NMR (400 MHz, CDCI3) delta 1.35-1.47 (m, 3H), 2.34 (s, 3H), 2.47-2.60 (m, 4H), 3.60-3.71 (m, 4H), 4.37-4.47 (m, 2H), 5.30 (s, 1H). |
| 73% | With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 3.0h; | A solution of compound 7A (60 g, 0.313 mol), K2C03 (130 g, 0.94 mol), and methyl piperazine in DMF (300 mL) was stirred at 40 C for 3 h. The reaction mixture was poured into water and extracted with CH2C12. The organic layer was washed with water, dried over Na2S04, and concentrated to give compound 7B (58.5 g, 73%) as a yellow solid. 1H NMR (400 MHz, CDC13) delta 4.37-4.47 (m, 2H), 3.60-3.71 (m, 4H), 2.47-2.60 (m, 4H), 2.34 (s, 3H), 1.35- 1.47 (m, 3H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 44% | With toluene-4-sulfonic acid; In ethanol;Reflux; | [0192] Step 3. A mixture of Compound 6-D (4.1 g, 0.015 mol), Compound 6-E (2.33 g, 0.0 13 mol) and p-toluenesulfonic acid (2.85 g, 0.0 15 mol) in ethanol (70 mL) was refluxed overnight. Monitoring by thin layer chromatography (petrol ether: ethyl acetate=2: 1 and Rf at 0.5) showed the reaction was complete. The mixture was partitioned between saturated aqueous NaHCO3 (100 mL) and ethyl acetate (100 mL) and extracted with ethyl acetate (100 mL x 2). The combined organic layers were dried and concentrated. The residue was recrystallized with ethyl acetate to give Compound 6-F (2.8 g, 44%) as light brown solid.?H NMR (400 MHz, MeOH) oe 1.37-1.41 (m, 3H), 4.40-4.48 (m, 2H), 7.42-7.47 (m, 2H), 7.78-7.87 (m, 4H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 0.95 g | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 7.5h;Inert atmosphere; | Reference Production Example 2 (0648) 5-Chloro-1,3,4-thiadiazole-2-carboxylic acid ethyl ester (1.00 g, 5.19 mmol), 1-pentyne (530 mg, 7.79 mmol), triethylamine (2.9 mL, 20.8 mmol), copper iodide (20 mg, 0.10 mmol) and dichlorobis(triphenylphosphine)palladium (73 mg, 0.10 mmol) were added, and the mixture was stirred at room temperature for 7 hours and 30 minutes, under a nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with aqueous ammonia, 1.5% hydrochloric acid and saturated saline water, and then dried over anhydrous sodium sulfate. The residue was applied to a silica gel column chromatography to obtain 0.95 g of ethyl 5-pent-1-ynyl-1,3,4-thiadiazole-2-carboxylate represented by the following formula. 1H-NMR(CDCl3, TMS)delta(ppm) :1.07(t, 3H), 1.46(t, 3H), 1.70(m, 2H), 2.51(t, 2H), 4.52(q, 2H) |

[ 64837-49-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 51% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; | To a stirred solution of <strong>[64837-49-6]ethyl 5-chloro-1 ,3,4-thiadiazole-2-carboxylate</strong> (0.25 g, 1 .29mmol) in dry DMF (2.5 mL), K2C03 (0.54 g, 3.89 mmol) and Intermediate 30 (0.59 g,1 .93 mmol) were added at rt. The reaction mixture was stirred overnight at 80 C. It was then concentrated under vacuum. EtOAc (10 mL) was added and the resulting solution was washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by flash chromatography to afford thetitle compound. Yield: 51% (0.26 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 67.15 (d, J= 7.60 Hz, IH), 6.75 (d, J= 7.60 Hz, IH), 6.71 (s, IH), 4.50 (t, J= 8.80 Hz,2H), 4.33 (q, J = 6.80 Hz, 2H), 3.54 (t, J= 5.20 Hz, 4H), 3.43-3.41 (m, IH), 3.13 (t, J=8.40 Hz, 2H), 2.45-2.32 (m, 4H), 1.31-1.27 (m, 6H). LCMS: (Method A) 389.2 (M+H),Rt. 2.88mm, 95.7% (Max). HPLC: (Method A) Rt2.8lmin, 96.5% (Max). |
| 0.26 g | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; | To a stirred solution of <strong>[64837-49-6]ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate</strong> (0.25 g, 1.29 mmol) in dry DMF (2.5 mL), K2CO3 (0.54 g, 3.89 mmol) and Example 8 (0.59 g, 1.93 mmol) were added at rt. The reaction mixture was stirred overnight at 80 C It was then concentrated under vacuum. EtOAc (10 mL) was added and the resulting solution was washed with water (10 mL), brine(10 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by flash chromatography to afford the title compound. Yield: 51% (0.26 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 7.15 (d, J = 7.60 Hz, 1H), 6.75 (d, J = 7.60 Hz, 1H), 6.71 (s, 1H), 4.50 (t, J = 8.80 Hz, 2H), 4.33 (q, J = 6.80 Hz, 2H), 3.54 (t, J= 5.20 Hz, 4H), 3.43-3.41 (m, 1H), 3.13 (t, J= 8.40Hz, 2H), 2.45-2.32 (m, 4H), 1.31-1.27 (m, 6H). LCMS: (Method A) 389.2(M+H), Rt. 2.88min, 95.7% (Max). HPLC: (Method A) Rt 2.81min, 96.5% (Max). |

[ 64837-49-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 51% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; | To a stirred solution of <strong>[64837-49-6]ethyl 5-chloro-1 ,3,4-thiadiazole-2-carboxylate</strong> (0.25 g, 1 .29 mmol) in dry DMF (2.5 mL), K2C03 (0.54 g, 3.89 mmol) and Intermediate 13 (0.59 g, 1.93 mmol)were added at rt. The reaction mixture was stirred overnight at 80 C. It was then concentrated under vacuum. EtOAc (10 mL) was added and the resulting solution waswashed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4 and concentrated.The crude product was purified by flash chromatography to afford the title compound.Yield: 51% (0.26 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 6 7.15 (d, J = 7.60 Hz,IH), 6.75 (d, J = 7.60 Hz, IH), 6.71 (5, IH), 4.50 (t, J = 8.80 Hz, 2H), 4.33 (q, J = 6.80 Hz,2H), 3.54 (t, J = 5.20 Hz, 4H), 3.43-3.41 (m, IH), 3.13 (t, J = 8.40 Hz, 2H), 2.45-2.32 (m,4H), 1.31-1.27 (m, 6H). LCMS: (Method A) 389.2 (M+H), Rt. 2.88mm, 95.7% (Max). HPLC:(Method A) Rt 2.81 mm, 96.5% (Max). |
| 51% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; | To a stirred solution of <strong>[64837-49-6]ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate</strong> (0.25 g, 1.29 mmol) in dry DMF (2.5 mL), K2CO3 (0.54 g, 3.89 mmol) and Intermediate 13 (0.59 g, 1.93 mmol) were added at rt. The reaction mixture was stirred overnight at 80 C. It was then concentrated under vacuum. EtOAc (10 mL) was added and the resulting solution was washed with water (10 mL), brine (10 mL), dried over anhydrous Na2S04 and concentrated. The crude product was purified by flash chromatography to afford the title compound. Yield: 51 % (0.26 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 7.15 (d, J = 7.60 Hz, 1 H), 6.75 (d, J = 7.60 Hz, 1 H), 6.71 (s, 1 H), 4.50 (t, J = 8.80 Hz, 2H), 4.33 (q, J = 6.80 Hz, 2H), 3.54 (t, J = 5.20 Hz, 4H), 3.43-3.41 (m, 1 H), 3.13 (t, J = 8.40 Hz, 2H), 2.45-2.32 (m, 4H), 1.31 -1.27 (m, 6H). LCMS: (Method A) 389.2 (M+H), Rt. 2.88min, 95.7% (Max). HPLC: (Method A) Rt 2.81 min, 96.5% (Max). |

[ 64837-49-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | With triethylamine; In N,N-dimethyl-formamide; at 0 - 100℃; | To a stirred solution of Intermediate 2 (2.62 g, 9.40 mmol) in dry DMF (25 mL), TEA (2.8 mL, 20.15 mmol) and <strong>[64837-49-6]ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate</strong> (1.2 g, 6.71 mmol) were added at 0 C. The reaction mixture was stirred at 100 C overnight. The reaction mixture was concentrated under vacuum. The resulting crude mixture was dissolved inDCM (35 mL), washed with water (20 mL) and dried over Na2SO4. After evaporation of thesolvent, the resulting product was triturated in Et20 (2 x 4 mL), affording the titlecompound. Yield: 50% (1.3 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 68.93 (d, J= 6.0 Hz, 2H), 8.09 (d, J = 8.8 Hz, IH), 8.01 (5, IH), 7.91 (d, J = 8.8 Hz, IH), 4.33 (q, J =7.2 Hz, 2H), 3.85 (t, J = 6.0 Hz, IH), 3.58 (5, 4H), 2.70-2.58 (m, 2H), 2.58-2.50 (m, 2H),1.44 (d, J = 6.4 Hz, 3H), 1.29 (t, J = 6.80 Hz, 3H). LCMS: (Method A) 399.2 (M+H), Rt.2.22 mm, 96.96% (Max). HPLC: (Method A) Rt 2.27 mm, 96.97% (Max). |

[ 64837-49-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | With triethylamine; In N,N-dimethyl-formamide; at 0 - 100℃; | To a stirred solution of Intermediate 2 (2.62 g, 9.40 mmol) in dry DMF (25 mL), TEA (2.8 mL, 20.15 mmol) and <strong>[64837-49-6]ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate</strong> (1.2 g, 6.71 mmol) were added at 0 C. The reaction mixture was stirred at 100 C overnight. The reaction mixture was concentrated under vacuum. The resulting crude mixture was dissolved in DCM (35 mL), washed with water (20 mL) and dried over Na2SO4. After evaporation of the solvent, the resulting product was triturated in Et20 (2 x 4 mL), affording the title compound. Yield: 50% (1.3 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 8.93 (d, J = 6.0 Hz, 2H), 8.09 (d, J = 8.8 Hz, 1 H), 8.01 (s, 1 H), 7.91 (d, J = 8.8 Hz, 1 H), 4.33 (q, J = 7.2 Hz, 2H), 3.85 (t, J = 6.0 Hz, 1 H), 3.58 (s, 4H), 2.70-2.58 (m, 2H), 2.58-2.50 (m, 2H), 1.44 (d, J = 6.4 Hz, 3H), 1.29 (t, J = 6.80 Hz, 3H). LCMS: (Method A) 399.2 (M+H), Rt. 2.22 min, 96.96% (Max). HPLC: (Method A) Rt 2.27 min, 96.97% (Max). |
[ 33216-53-4 ]
[ 64837-49-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 69% | With potassium carbonate; In N,N-dimethyl-formamide; at 65℃; for 2.0h;Inert atmosphere; | A mixture of <strong>[64837-49-6]ethyl 5-chloro-1 ,3,4-thiadiazole-2-carboxylate</strong> (2.31 g, 12.00 mmol) and 3,5-dichloropyridine-4-thiol (2.484 g, 13.80 mmol) in DMF (48 mL) was treated with K2CO3 (3.65 g, 26.4 mmol). The reaction mixture was stirred at 65QC for 2 h. The reaction was cooled to room temperature, quenched with H2O, and extracted with EA. The combined organic extracts were washed with H2O and brine, dried over Na2SO4. The solvent was removed and the residue was purified by flash column (Hex:EA = 5:1 ) to afford 2.776 g (69%) of ethyl 5-((3,5-dichloropyridin-4-yl)thio)-1 ,3,4-thiadiazole-2- carboxylate as a yellow solid. 0.25 (Hex:EA = 4:1 ); HRMS (ESI) (m/z) [MH]+calcd for C10H8CI2N3O2S2, 335.9435, found 335.9205. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 79.9% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h; | 1. Synthesis of ethyl 5-(7-(t-butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-2-yl)-1,3,4-thiadiazole-2-carboxylate t-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate (249 mg, 1.1 mmol) was dissolved in 6 ml of DMF, to which were successively added anhydrous potassium carbonate (416 mg, 3.0 mmol) and ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate (193 mg, 1.0 mmol), and the mixture was allowed to react at 80 °C for 1.5 h. The reaction solution was cooled to room temperature, to which was added 20 ml of ethyl acetate. The reaction solution was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated to dryness under reduced pressure, and separated by thin layer chromatography, to provide the product ethyl 5-(7-(t-butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-2-yl)-1,3,4-thiadiazole-2-carboxylate (295 mg), with a yield of 79.9%, LC/MS (ESI+) calcd for C17H26N2O2S ([M+H]+) m/z 369.1. |
| 79.9% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h; | 1. Synthesis of ethyl 5-(7-(t-butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-2-yl)-1,3,4-thiadiazole-2-carboxylate t-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate (249 mg, 1.1 mmol) was dissolved in 6 ml of DMF, to which were successively added anhydrous potassium carbonate (416 mg, 3.0 mmol) and ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate (193 mg, 1.0 mmol), and the mixture was allowed to react at 80 °C for 1.5 h. The reaction solution was cooled to room temperature, to which was added 20 ml of ethyl acetate. The reaction solution was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated to dryness under reduced pressure, and separated by thin layer chromatography, to provide the product ethyl 5-(7-(t-butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-2-yl)-1,3,4-thiadiazole-2-carboxylate (295 mg), with a yield of 79.9%, LC/MS (ESI+) calcd for C17H26N2O2S ([M+H]+) m/z 369.1. |
| With potassium carbonate | 1 1. 1. Synthesis of ethyl 5-(7-(t-butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-2-yl)-1,3,4-thiadiazole-2-carboxylate t-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate (249 mg, 1.1 mmol) was dissolved in 6 ml of DMF, to which were successively added anhydrous potassium carbonate (416 mg, 3.0 mmol) and ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate (193 mg, 1.0 mmol), and the mixture was allowed to react at 80 °C for 1.5 h. The reaction solution was cooled to room temperature, to which was added 20 ml of ethyl acetate. The reaction solution was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated to dryness under reduced pressure, and separated by thin layer chromatography, to provide the product ethyl 5-(7-(t-butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-2-yl)-1,3,4-thiadiazole-2-carboxylate (295 mg), with a yield of 79.9%, LC/MS (ESI+) calcd for C17H26N2O2S ([M+H]+) m/z 369.1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 12 % | With toluene-4-sulfonic acid In ethanol at 75℃; | 5-((1,4-Dimethyl-1H-pyrazol-3-yl)amino)-1,3,4-thiadiazole-2-carboxylic acid A mixture of ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate (97 mg, 0.504 mmol), 1,4- dimethyl-1H-pyrazol-3-amine (69 mg, 0.621 mmol) and 4-toluenesulfonic acid monohydrate (93 mg, 0.489 mmol) in Ethanol (2.5 mL) was heated at 75 °C for 22h. Aq. NaHCO3(2 mL) and EtOAc (2 mL) were added, the reaction mixture was filtered, the filtrate mixture was extracted with EtOAc (2 × 5 mL). The organic layers were washed with brine (5 mL), combined, dried (Na2SO4) and evaporated. The crude material was purified by column chromatography over silica (4 g cartridge) eluting with a gradient of EtOAc (10% to 100%; v/v) in isohexane to give ethyl 5-[(1,4- dimethylpyrazol-3-yl)amino]-1,3,4-thiadiazole-2-carboxylate (16 mg, 12% yield) as an off-white solid. MS (ES+) m/z = 268.2 [M+H]+.1H NMR (400MHz, DMSO-d6) δ 11.46 (s, 1H), 7.47 (s, 1H), 4.36 (q, J = 7.1 Hz, 2H), 3.75 (s, 3H), 2.00 (d, J = 0.8 Hz, 3H), 1.33 (t, J = 7.1 Hz, 3H). |

A142073 [64837-53-2]
Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate
Similarity: 0.72

A293805 [1030613-07-0]
Ethyl 5-bromo-1,3,4-thiadiazole-2-carboxylate
Similarity: 0.69

A142073 [64837-53-2]
Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate
Similarity: 0.72

A293805 [1030613-07-0]
Ethyl 5-bromo-1,3,4-thiadiazole-2-carboxylate
Similarity: 0.69

A307899 [15884-86-3]
5-(Methoxymethyl)-1,3,4-thiadiazol-2-amine
Similarity: 0.52