Structure of 916317-00-5
*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. : | 916317-00-5 |
| Formula : | C7H16ClNO |
| M.W : | 165.66 |
| SMILES Code : | Cl.COCC1CCNCC1 |
| English Name : | 4-(Methoxymethyl)piperidine hydrochloride |
| MDL No. : | MFCD08062602 |
| InChI Key : | FLRDPZJPRQWKLD-UHFFFAOYSA-N |
| Pubchem ID : | 17218599 |
| Num. heavy atoms | 10 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 1.0 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 48.42 |
| TPSA ? Topological Polar Surface Area: Calculated from |
21.26 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.2 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.05 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.9 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.38 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.91 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-1.49 |
| Solubility | 5.35 mg/ml ; 0.0323 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-1.24 |
| Solubility | 9.47 mg/ml ; 0.0572 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.58 |
| Solubility | 4.33 mg/ml ; 0.0261 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 |
-6.46 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) |
1.21 |
* 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 |
|---|---|---|
| With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran; methanol at 20℃; | 26 Example 26 3'-({4-[(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy)methyl)-2-methylbiphenyl-4-carboxylic acid (10.8 mg) was dissolved in a THF-methanol [1 ml, 4:1 (v/v)] mixed solution, and the solution was added to 4-(methoxymethyl)piperidine hydrochloride (7.5 mg). DMT-MM (12 mg) and triethylamine (20 µl) were added, followed by overnight stirring at room temperature. Thereafter, chloroform was added to the reaction liquid, and the organic layer was washed with 1 M hydrochloric acid. The organic layer was concentrated, and the residue was purified by a fractional HPLC (Waters, product name: Waters SunFire Prep C18OBD (1.9 x 100 mm, 5 µm)) to obtain 2-{4-[(4'-[4-(methoxymethyl)piperidin-1-yl]carbonyl)-2'-methylbiphenyl-3-yl)methoxy]benzyl}-1,2,4-oxadiazolidine-3,5-dione (9.0 mg). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 47% | Stage #1: N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide; 4-(methoxymethyl)piperidine hydrochloride In N,N-dimethyl-formamide at 100℃; for 1h; Stage #2: With triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; Stage #3: trifluoroacetic acid In water; acetonitrile HPLC; | 240 N-(7-chloro-2-methylpyrazolo[ 1 ,5-α]pyrimidin-5-yl)-4-(2-hydroxypropan-2- yl)benzamide (2F, 0.05g, 1.0 equivalent) and 4-(methoxymethyl)piperidine HCl salt (1.6 equivalents) in DMF (0.1M) was heated to 100 0C for Ih. Then Et3N (6.0 equivalents) was added and the mixture was heated to 80 0C for 8 h. The solvent was removed in vacuo and the crude mixture was purified by preparatory HPLC (20-45% ACN/water, TFA mode) to afford the TFA salt of the titled compound 226 (47%) as a beige solid. 1H NMR (400 MHz, DMSO-J6) δ ppm l.39 (dd, J=12.38, 3.54 Hz, 2 H) 1.44 (s, 6 H) 1.81 (d, J= 16.42 Hz, 2 H) 1.89 (br. s., 1 H) 2.36 (s, 3 H) 2.94 - 3.10 (m, 2 H) 3.24 (s, 2 H) 3.26 (s, 3 H) 4.44 (br. s., 2 H) 6.14 (s, 1 H) 7.30 (s, 1 H) 7.59 (m, 2 H) 7.98 (m, 2 H) 10.81 (s, 1 H); ESI-MS: m/z 438.2 (M+H)+. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 41% | Stage #1: tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 20h; Stage #3: With hydrogenchloride In 1,4-dioxane for 20h; | 94.a EXAMPLE 94A/-methyl-4-{4-[(methyloxy)methyl]-1-piperidinyl}-3-(1 /-/-purin-6- ylamino)benzenesulfonamidea) 4-[(methyloxy)methyl]piperidine hydrochlorideTo a solution of 1 , 1 -dimethylethyl 4-(hydroxymethyl)-1 -piperidinecarboxylate (1 .0 g, 4.64 mmol) in THF (20 mL) was added NaH (60% dispersion in oil, 0.279 g, 6.97 mmol). After the mixture was stirred at 25 °C for 1 h, iodomethane (0.581 mL, 9.29 mmol) was added. The mixture was stirred at rt for 20 h, concentrated, and purified by flash column chromatography (5-80% EtOAc/hexanes) to afford a colorless oil which was redissolved into CH2CI2 (5 mL) and treated with 2 M HCI in 1 ,4-dioxane (1 1 .61 mL, 23.22 mmol). The mixture was stirred for another 20 h and concentrated to afford the title compound (313.5 mg, 41 %) as a white solid. LCMS (ES) m/z 130 (M+H)+; 1H NMR (400 MHz, DMSO-de) δ ppm 1 .28 - 1 .48 (m, 2 H) 1 .67 - 1 .85 (m, 3 H) 2.81 (br. s, 2 H) 3.17 (d, J=6.32 Hz, 3 H) 3.19 - 3.27 (m, 4 H) 8.94 (br. s, 1 H) 9.21 (br. s, 1 H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: triethylamine / 20 h / 110 °C / Sealed vessel 2: hydrogen / palladium on activated charcoal / ethanol / 0.67 h / 1810.07 Torr 3: acetic acid / 1,4-dioxane / 20 h / 110 °C / Sealed tube |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: triethylamine / 20 h / 110 °C / Sealed vessel 2: hydrogen / palladium on activated charcoal / ethanol / 0.67 h / 1810.07 Torr |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | With triethylamine at 110℃; for 20h; Sealed vessel; | 94.b b) A/-methyl-4-{4-[(methyloxy)meth l]-1-piperidinyl}-3-nitrobenzenesulfonamideTo a solution of 4-fluoro-/V-methyl-3-nitrobenzenesulfonamide (150 mg, 0.64 mmol) and Et3N (1.92 mmol) was added 4-[(methyloxy)methyl]piperidine hydrochloride (127 mg, 0.77 mmol). The reaction vessel was sealed and heated at 1 10 °C for 20 h. The mixture was concentrated and purified by flash column chromatography (5-80%EtOAc/hexanes) to afford the title compound (164.1 mg, 75%) as a yellow oil. LCMS (ES) m/z 344 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (d, J=1 1 .62 Hz, 2 H) 1.73 (d, J=12.88 Hz, 3 H) 2.41 (d, J=5.05 Hz, 3 H) 2.98 (br. s, 2 H) 3.18 - 3.28 (m, 5 H) 3.39 (br. s, 2 H) 7.42 (d, J=8.84 Hz, 1 H) 7.48 (d, J=5.05 Hz, 1 H) 7.79 (dd, J=8.84, 2.27 Hz, 1 H) 8.1 1 (d, J=2.02 Hz, 1 H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 180 mg | With triethylamine In ethanol at 55℃; for 2h; | Y.1.iii iii) 2-[5-(4-fluorophenyl)-4-[4-(methoxymethyl)- 1 -piperidyl]thieno[2,3-d]pyrimidin-2- yl] ethanol iii) 2-[5-(4-fluorophenyl)-4-[4-(methoxymethyl)- 1 -piperidyl]thieno[2,3-d]pyrimidin-2- yl] ethanol2-[4-Chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-yl]ethanol (150 mg, 0.0005 mol), triethylamine (0.214 mL, 0.00154 mol) and 4-(methoxymethyl)piperidine hydrochloride (0.091 g, 0.00055 mol) were dissolved in ethanol (5 mL) and warmed to 55 °C for 2 hrs. The reaction was then poured over ice and extracted with DCM. The organics were dried by passage through a PTFE frit and concentrated in vacuo to give 2-[5-(4-fluorophenyl)-4-[4- (methoxymethyl)-l-piperidyl]thieno[2,3-d]pyrimidin-2-yl] ethanol (180 mg). LCMS RT = 4.33min. M+l = 402. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylamine In ethanol at 65 - 150℃; for 6.16h; Microwave irradiation; | Y.2.i i) 2-[4-[4-(methoxymethyl)- 1 -piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2yl]acetic acid i) 2-[4-[4-(methoxymethyl)- 1 -piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2yl]acetic acidEthyl 2-(4-chloro-5-phenyl-thieno[2,3-d]pyrimidin-2-yl)acetate (100 mg, 0.285 mmol), 4- (methoxymethyl)piperidine hydrochloride (52 mg, 0.314 mmol) and triethylamine (0.12 mL, 0.85 mmol) were dissolved in ethanol (4 mL) and heated to 65 °C for 6 hrs. The reaction was then heated to 150 °C in a microwave for 10 min. The reaction was poured over ice and ectracted with DCM. The extracts were combined and concentrated in vacuo. The residue was dissolved in non-dry THF (2 mL) and lithium hydroxide monohydrate (48 mg) was added. The reaction was stirred at room temperature overnight then another portion of lithium hydroxide monohydrate was added (10 mg) and the reaction stirred for a further 2 hrs. The reaction mixture was purified on an Isolute NH2 SPE column (eluting ammonia in methanol) to give 2-[4-[4-(methoxymethyl)-l-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin- 2yl] acetic acid (107 mg). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium hydrogencarbonate; potassium iodide In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; | Synthesis of intermediate BF01: potassium -(methoxymethyl)piperidin-1-yljmethyl}borate 4-(Methoxymethyl)piperidine hydrochloride ([916317-00-5], 1.0 g, 6.03 mmol), potassium bromomethyl trifluoroborate (1.21 g, 6.03 mmol), KHCO3 (1.2 g, 12.1 mmol) and KI (100 mg, 0.6 mmol) were stirred under N2 in dry THF (8 mL) at 80 °C for 4 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was suspended in dry acetone and filtered. The filtrate was treated with diethyl ether, and the resulting precipitate was collected by filtration and dried to afford the titled compound, which was used as such in the next step. | |
| With potassium hydrogencarbonate; potassium iodide In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; | Synthesis of intermediate BF01: potassium -(methoxymethyl)piperidin-1-yl]methyl}borate 4-(Methoxymethyl)piperidine hydrochloride ([916317-00-5], 1.0 g, 6.03 mmol,), potassium bromomethyl trifluoroborate (1.21 g, 6.03 mmol), KHCO3 (1.2 g, 12.1 mmol) and KI (100 mg, 0.6 mmol) were stirred under N2 in dry THF (8 mL) at 80° C. for 4 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was suspended in dry acetone and filtered. The filtrate was treated with diethyl ether, and the resulting precipitate was collected by filtration and dried to afford the titled compound, which was used as such in the next step. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 20h; | Illustrative synthesis of E092: methyl 1-(4-fluorophenyl)-3-isopropyl-4-[4-(methoxymethyl)-1-piperidyl]pyrazolo[3,4-b]pyridine-6-carboxylate General procedure: A mixture of HP05 (6.71 g, 19.29 mmol, 1.0 equiv), 4-(methoxymethyl)piperidine hydrochloride (CAS 916317-00-5, 6.39 g, 38.58 mmol, 2 equiv) and DIPEA (10.1 mL, 57.88 mmol, 3 equiv) in anhydrous DMSO (65 mL) was heated at 100° C. for 20 h. The reaction mixture was cooled to RT, partitioned between ethyl acetate (300 mL) and a mixture of water and a saturated solution of NaCl 1:1 (300 mL). The two phases were separated, and the aqueous phase was extracted with ethyl acetate (150 mL). The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude mixture was purified by flash chromatography on silica gel eluting with n-heptane/ethyl acetate to afford the titled compound |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 4-(methoxymethyl)piperidine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.0833333h; Cooling with ice; Inert atmosphere; Stage #2: benzyl N-chlorosulfonylcarbamate In dichloromethane at 20℃; for 3h; | 2 Step 2: benzyl [4-(methoxymethyl)piperidine-1-sulfonyl] carbamate A solution of 4-(methoxymethyl)piperidine hydrochloride ([399580-55-3], 1.0 g, 6.0 mmol) and N,N-diisopropylethylamine (2.3 mL, 13.3 mmol) in anhydrous DCM (10 mL) was cooled down in an ice bath under an argon atmosphere. Benzyl (chlorosulfonyl)carbamate from Step 1 (1.8 g, 7.2 mmol) was added and after 5 minutes, and the solution was allowed to warm up to RT. After 3 hours, water (10 mL) and DCM (10 mL) were added, and stirring was continued for 15 minutes. The organic phase was separated, washed successively with an aqueous 1 M HCl solution (2 x 10 mL), and a saturated aqueous solution of NaCl (10 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with a gradient of DCM/MeOH to give the titled compound. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 20h; | Synthesis of E092: methyl 1-(4-fluorophenyl)-3-isopropyl-4-[4-(methoxymethyl)-1-piperidyl]pyrazolo[3,4-b]pyridine-6-carboxylate A mixture of HP05 (6.71g, 19.29 mmol, 1.0 equiv), 4-(methoxymethyl)piperidine hydrochloride (CAS 916317-00-5, 6.39g, 38.58 mmol, 2 equiv) and DIPEA (10.1 mL, 57.88 mmol, 3 equiv) in anhydrous DMSO (65 mL) was heated at 100 °C for 20 h. The reaction mixture was cooled to RT, partitioned between ethyl acetate (300 mL) and a mixture of water and a saturated solution of NaCl 1 : 1 (300 mL). The two phases were separated, and the aqueous phase was extracted with ethyl acetate (150 mL). The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude mixture was purified by flash chromatography on silica gel eluting with n-heptane/ethyl acetate to afford the titled compound. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: potassium iodide; potassium hydrogencarbonate / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 2: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; water / 80 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 71% | With methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II); sodium t-butanolate; ruphos In tetrahydrofuran at 85℃; for 24h; Inert atmosphere; Glovebox; |

A145756 [955400-18-7]
(R)-3-(Methoxymethyl)pyrrolidine hydrochloride
Similarity: 0.83

A164137 [535924-74-4]
(S)-3-(Methoxymethyl)pyrrolidine
Similarity: 0.79

A138414 [3970-73-8]
4-Methoxy-4-methylpiperidine hydrochloride
Similarity: 0.77

A125615 [1185088-10-1]
2-(2-Methoxyethyl)piperidine hydrochloride
Similarity: 0.77

A260396 [4045-25-4]
4-Methoxypiperidine hydrochloride
Similarity: 0.73

A1483770 [479195-19-2]
2-Oxa-8-azaspiro[4.5]decane hydrochloride
Similarity: 0.90

A181783 [374795-37-6]
2-Oxa-7-azaspiro[4.5]decane hydrochloride
Similarity: 0.84

A190231 [1125551-75-8]
(S)-Piperidin-3-ylmethanol hydrochloride
Similarity: 0.82

A115570 [297172-16-8]
(4-Methylpiperidin-4-yl)methanol
Similarity: 0.81