Structure of 145742-50-3
*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 !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
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) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
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) ]}
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
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
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. : | 145742-50-3 |
Formula : | C8H8ClNO2 |
M.W : | 185.61 |
SMILES Code : | O=CC1=CC(Cl)=C(N)C=C1OC |
MDL No. : | MFCD24645097 |
InChI Key : | FRPLOCDKNDMVOD-UHFFFAOYSA-N |
Pubchem ID : | 53646819 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 47.74 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.63 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.3 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.75 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.09 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.9 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.54 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.05 |
Solubility | 1.66 mg/ml ; 0.00896 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.0 |
Solubility | 1.86 mg/ml ; 0.01 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.73 |
Solubility | 0.344 mg/ml ; 0.00185 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 |
Yes |
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) |
No |
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 |
-6.51 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 |
2.0 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) |
1.42 |
* 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 |
---|---|---|
80% | Step B: Preparation of 4-Amino-5-chloro-2-methoxybenzaldehydeIsopropylmagnesium chloride (2M in tetrahydrofuran, 23 ml, 46 mmol) (commercially available, for example, from Aldrich) was added over 5 minutes to a stirred solution of 4-bromo-2-chloro-5-methoxyaniline (Step A) (10 g, 42 mmol) in tetrahydrofuran (70 ml) at -10 C. The resulting solution was allowed to warm to 0 C. over 50 minutes to give a thick slurry, then cooled to -25 C. and n-butyllithium (1.6M in hexanes, 90 ml, 144 mmol) was added over 20 minutes followed by tetrahydrofuran (20 ml). The solution was warmed to -10 C. over 30 minutes and then N,N-dimethylformamide (16 ml, 207 mmol) was added over 5 minutes and the resulting thick slurry was warmed to 0 C. over 20 minutes. A solution of citric acid (22 g, 105 mmol) in water (50 ml) was added cautiously over 15 minutes keeping reaction at <10 C. The slurry was aged at 20 C. for 30 minutes then filtered under vacuum. The cake was washed with water (100 ml) and then dried under vacuum at 40 C. for 16 hours to give 4-amino-5-chloro-2-methoxybenzaldehyde (6.1 g, 80% th) as a pale yellow solid.1H NMR (400 MHz, DMSO-d6) deltaH (ppm) 9.95 (1H, s), 7.49 (1H, s), 6.50-6.57 (2H, br s), 6.44 (1H, s), 3.81 (3H, s)m/z (ES+) 186 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃; for 2.5h; | Preparation 23-Chloropropionyl chloride (98.4 ml, 1.0 mol) was added over 30 minutes to a stirred suspension of <strong>[145742-50-3]4-amino-5-chloro-2-methoxybenzaldehyde</strong> (47.4 g, 0.26 mol) ensuring the reaction temperature did not exceed 20 C. After the addition was complete the reaction was stirred at 20 C. for a further 2 hours and then filtered. The filtrate was concentrated to 150 ml under reduced pressure and then diluted with ethyl acetate (100 ml) and water (400 ml). The mixture was stirred at 20 C. for 1 hour and then filtered to give 3-chloro-N-[2-chloro-4-formyl-5-(methyloxy)phenyl]propanamide as an off-white solid which was not isolated but suspended in tetrahydrofuran (730 ml) and treated with diisopropylethylamine (154 ml, 0.88 mol). The resulting mixture was stirred at 45 C. for 46 hours and then concentrated under reduced pressure to leave a residue which was diluted with ethyl acetate (300 ml), washed with 2M hydrochloric acid (4×100 ml) and concentrated under reduced pressure to give N-[2-chloro-4-formyl-5-(methyloxy)phenyl]-2-propenamide (37.8 g, 62%).1H NMR (400 MHz, CDCl3) deltaH (ppm) 10.31 (1H, s), 8.43 (1H, s), 8.02 (1H, br s), 7.82 (1H, s), 6.47-6.53 (1H, dd), 6.28-6.38 (1H, dd), 5.88-5.93 (1H, dd), 3.96 (3H, s)m/z (ES+) 240 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; at 25 - 40℃; for 1.5h; | Step C: Preparation of N-[2-chloro-4-formyl-5-(methyloxy)phenyl]-2-propenamidePreparation 1Acrylic acid (commercially available, for example, from Aldrich) (46 ml, 0.67 mol) was added slowly to a stirred suspension of <strong>[145742-50-3]4-amino-5-chloro-2-methoxybenzaldehyde</strong> (Step B) (50.0 g, 0.27 mol) and triethylamine (204 g, 2.02 mol) in ethyl acetate (0.85 L) at 25 C. Propanephosphonic anhydride (50% in ethyl acetate; 429 g, 0.67 mol) was added over 30 minutes keeping reaction temperature at 30-40 C. The mixture was stirred at 30-40 C. for a further 1 hour and then cooled to 25 C. and diluted with water (0.26 L) and acidified with 32% hydrochloric acid (108 g) to pH 2-3. The organic layer was separated and washed with a mixture of water (0.23 L) and 32% sodium hydroxide (14 g)-aqueous layer ca. pH 7. The organic phase was washed with water (0.23 L) and then concentrated under reduced pressure (ca. 300 mbar) to remove 0.56 kg of distillate. Methylcyclohexane (335 g) was added and then a further 286 g of distillate was removed under reduced pressure. Methylcyclohexane (111 g) was added and then the resulting suspension was cooled to 20 C., filtered and washed with methylcyclohexane. The cake was dried at 40 C. under reduced pressure for 12 hours to give N-[2-chloro-4-formyl-5-(methyloxy)phenyl]-2-propenamide (46 g, 71%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<strong>[145742-50-3]4-amino-5-chloro-2-methoxybenzaldehyde</strong> (3a) (462 mg, 2.49 mmol) was dissolved in 49 toluene (15 ml), 50 triethylamine (630 mg, 6.22 mmol) was added thereto, and then 51 triphosgene (554 mg, 1.87 mmol) was added under N2 protection, followed by a reaction at 120C for 1 hour. After cooling to room temperature, Reaction Solution 1 was obtained. 44 Tert-butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate (4B) (500 mg, 2.49 mmol) was dissolved in 13 tetrahydrofuran (15 ml), to which triethylamine (630 mg, 6.22 mmol) and then Reaction Solution 1 were added, followed by a reaction at 85C for 3 hours. The reaction solution was cooled to room temperature, and water (50 ml) was added thereto, which was extracted with ethyl acetate (100 mL×2). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, to obtain 46 tert-butyl (3R)-3-[(2-chloro-4-formyl-5-methoxy-phenyl)carbamoyloxymethyl] pyrrolidine-1-carboxylate (4C) as a brown liquid, which was directly used in the next step without purification. LCMS m/z =451.4[M+39]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | <strong>[145742-50-3]4-amino-5-chloro-2-methoxybenzaldehyde</strong> (3a) (6.9 g, 37.2 mmol) was dissolved in toluene (100 ml), to which triphosgene (5.51 g, 18.6 mmol) was added, followed by a reaction at 120C for 2 hours, and the resultant was concentrated to obtain Reaction solution 1. Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (2a) (2.00 g, 9.29 mmol) was dissolved in tetrahydrofuran (50 ml), to which Reaction solution 1 and then triethylamine (3.76 g, 37.2 mmol) were added, followed by a reaction at 70C for 2 hours. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether (v/v) = 1:9 to 3:7) to give yellow oily tert-butyl 4-[(2-chloro-4-formyl-5-methoxy-phenyl)carbamoyloxymethyl]piperidine-1-carboxyl ate (3b) (2.2 g, yield: 74%). 1H NMR (400 MHz, CDCl3) delta 10.29 (s, 1H), 8.05 (s, 1H), 7.83 (s, 1H), 7.41 (s, 1H), 4.16 (d, 2H), 4.09 (d, 2H), 3.95 (s, 3H), 2.73 (m, 2H), 1.96 - 1.83 (m, 1H), 1.75 (d, 2H), 1.46 (s, 9H), 1.32 - 1.18 (m, 2H). LCMS m/z =449.3 [M+23]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4-amino-5-chloro-2-methoxybenzaldehyde (3a) (1.38 g, 7.45 mmol) was dissolved in 49 toluene (15 ml), 50 triethylamine (0.75 g, 7.45 mmol) was added thereto, and then 51 bis(trichloromethyl)carbonate (1.1 mg, 3.72 mmol) was added under N2 protection, followed by a reaction at 120C for 1 hour. A reaction solution was obtained after cooling to room temperature. 69 Tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate (5B) (0.6 g, 2.98 mmol) was dissolved in 13 tetrahydrofuran (15 ml), to which triethylamine (0.75 g, 7.45 mmol) and the reaction solution were added, followed by a reaction at 85C for 3 hours. The reaction solution was cooled to room temperature, and water (50 ml) was added thereto, which was extracted with ethyl acetate (100 mL×2).The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, to obtain 74 tert-butyl (3S)-3-[(2-chloro-4-formyl-5-methoxy-phenyl)carbamoyloxymethyl]pyrrolidine-1-car boxylate (5C) as a brown liquid, which was directly used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.3% | 4-Amino-5-chloro-2-methoxy-benzaldehyde (0.464 g, 2.50 mmol) and bis(trichloromethyl)carbonate (0.475 g, 1.60 mmol) were added to 1,4-dioxane. (20mL),The reaction was refluxed at 100 C for 3 hours.The solvent was removed under reduced pressure.The residue and 14A (0.381 g, 1.00 mmol) were added to THF (15 mL).Add triethylamine (0.253 g, 2.50 mmol),The reaction was refluxed for 2 hours.Cool to room temperature,The solvent was removed under reduced pressure.The residue was purified by silica gel column chromatography (dichloromethane/methanol (v/v) = 30:1).14B (0.500 g, yield 84.3%) was obtained as a yellow liquid. |
A121379 [7206-70-4]
4-Amino-5-chloro-2-methoxybenzoic acid
Similarity: 0.92
A100410 [108282-38-8]
4-Amino-5-chloro-2-ethoxybenzoic acid
Similarity: 0.89
A341511 [654084-41-0]
4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride
Similarity: 0.80
A359003 [4093-31-6]
Methyl 4-acetamido-5-chloro-2-methoxybenzoate
Similarity: 0.80
A701876 [220032-26-8]
4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide
Similarity: 0.80
A121379 [7206-70-4]
4-Amino-5-chloro-2-methoxybenzoic acid
Similarity: 0.92
A100410 [108282-38-8]
4-Amino-5-chloro-2-ethoxybenzoic acid
Similarity: 0.89
A341511 [654084-41-0]
4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride
Similarity: 0.80
A359003 [4093-31-6]
Methyl 4-acetamido-5-chloro-2-methoxybenzoate
Similarity: 0.80
A701876 [220032-26-8]
4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide
Similarity: 0.80
A258577 [7035-09-8]
5-Chloro-2-methoxybenzaldehyde
Similarity: 0.78
A112595 [29866-54-4]
2-Chloro-6-methoxybenzaldehyde
Similarity: 0.75
A236680 [90064-48-5]
4-Chloro-2,5-dimethoxybenzaldehyde
Similarity: 0.73
A182654 [55586-68-0]
4-(Diethylamino)-2-methoxybenzaldehyde
Similarity: 0.71
A129742 [635-93-8]
5-Chloro-2-hydroxybenzaldehyde
Similarity: 0.71
A121379 [7206-70-4]
4-Amino-5-chloro-2-methoxybenzoic acid
Similarity: 0.92
A100410 [108282-38-8]
4-Amino-5-chloro-2-ethoxybenzoic acid
Similarity: 0.89
A341511 [654084-41-0]
4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride
Similarity: 0.80
A359003 [4093-31-6]
Methyl 4-acetamido-5-chloro-2-methoxybenzoate
Similarity: 0.80
A701876 [220032-26-8]
4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide
Similarity: 0.80
A121379 [7206-70-4]
4-Amino-5-chloro-2-methoxybenzoic acid
Similarity: 0.92
A100410 [108282-38-8]
4-Amino-5-chloro-2-ethoxybenzoic acid
Similarity: 0.89
A341511 [654084-41-0]
4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride
Similarity: 0.80
A359003 [4093-31-6]
Methyl 4-acetamido-5-chloro-2-methoxybenzoate
Similarity: 0.80
A701876 [220032-26-8]
4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide
Similarity: 0.80