Home Cart Sign in  
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 3616-56-6 Chemical Structure| 3616-56-6

Structure of 3616-56-6

Chemical Structure| 3616-56-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 3616-56-6 ]

CAS No. :3616-56-6
Formula : C8H19NO2
M.W : 161.24
SMILES Code : CCOC(OCC)CN(C)C
MDL No. :MFCD00009232
InChI Key :SSFAUOAQOOISRQ-UHFFFAOYSA-N
Pubchem ID :77163

Safety of [ 3616-56-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 3616-56-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 6
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 45.64
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

21.7 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.74
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.87
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.95
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.82
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.6
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.2

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.99
Solubility 16.4 mg/ml ; 0.102 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.91
Solubility 19.9 mg/ml ; 0.123 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.5
Solubility 5.12 mg/ml ; 0.0318 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.67 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.26

Application In Synthesis of [ 3616-56-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3616-56-6 ]

[ 3616-56-6 ] Synthesis Path-Downstream   1~41

  • 1
  • [ 3616-56-6 ]
  • [ 52334-92-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 0 - 40℃; for 5h; Sodium 2-Dimethylamino-1-hydroxy-ethanesulfonate To a 5 L jacket reactor, (Dimethylamino)acetaldehyde diethyl acetal (400 g) and Water (200 mL) is charged at room temperature. Start agitation and cool the system down to 0 C., then Conc. HCl aqueous solution (37 wt %, 480 g) is added within 1 h, followed by stirring at 40 C. for 4 h. At this point, a solution of sodium metasulphite (424 g) in water (720 mL) is added into the above system within 40 min, and keep stirring at 40 C. for 2 h. The ethanol (2 L) is added and cool the mixture to 0 C., followed by filteration and washing with ethanol to get a white cake, which is dried in vacuo at 45 C. for 6 h to give desired compound 1 in 84% yield (474 g) and >98% NMR purity.
With hydrogenchloride; In water; at 0 - 40℃; for 12h;Inert atmosphere; Under the protection of N2, 6mol /l of HCl 11.7mL L of (0.07mol), cooled to 0 C, then dropwise added solution of (dimethylamino)acetaldehyde diethyl acetal 9.1mL (0. 05mol) then hydrolysis at 40 C for 12h, cooled to 0 C, the standby (stand by liquid A)
With hydrogenchloride; In water; at 30℃; 1 Concentrated hydrochloric acid plus purified water (1) after dilution,Transfer to a 10L reactorWarm up to about 30C. Under nitrogen protection,The dimethylamino acetaldehyde diethyl acetal was slowly added dropwise to the diluted hydrochloric acid,About 2 hours after the addition,The reaction was stirred overnight at about 30C. MakeBefore use, neutralize to neutral with solid sodium carbonate,Inorganic salts are filtered away.
With hydrogenchloride; In water; at 40℃; Concentrated hydrochloric acid (5 mL) and water (2 mL) were added to a 50mL of flask and then heated to 40C. N,N-<strong>[3616-56-6]dimethylaminoacetaldehyde diethyl acetal</strong> was added to the reaction flask and the mixture was stirred at 40C overnight.

  • 2
  • [ 3616-56-6 ]
  • [ 108372-22-1 ]
  • 3
  • (2,2-diethoxy-ethyl)-dimethyl-propyl-ammonium; iodide [ No CAS ]
  • [ 3616-56-6 ]
  • 5
  • [ 124-40-3 ]
  • [ 621-62-5 ]
  • [ 3616-56-6 ]
  • 7
  • [ 3616-56-6 ]
  • [ 57313-49-2 ]
  • [ 57313-42-5 ]
  • 8
  • [ 3616-56-6 ]
  • [ 4072-67-7 ]
  • [ 13717-24-3 ]
  • 9
  • [ 3616-56-6 ]
  • [ 57313-48-1 ]
  • [ 51211-09-7 ]
  • 10
  • [ 3616-56-6 ]
  • [ 946-03-2 ]
  • [ 57313-40-3 ]
  • 11
  • [ 3616-56-6 ]
  • [ 506-59-2 ]
  • [ 19289-58-8 ]
  • 13
  • [ 3616-56-6 ]
  • 1-Ethoxy-2-methylaminoethanol [ No CAS ]
  • 14
  • [ 3616-56-6 ]
  • 2-Dimethylamino-1-ethoxyethanol [ No CAS ]
  • 15
  • [ 3616-56-6 ]
  • [ 135-73-9 ]
  • [ 57313-51-6 ]
  • 16
  • [ 3616-56-6 ]
  • [ 68-12-2 ]
  • 1,3-Bis(dimethylamino)-2-ethoxytrimethinium perchlorate [ No CAS ]
  • 17
  • [ 3616-56-6 ]
  • [ 70-11-1 ]
  • [ 57313-41-4 ]
  • 18
  • [ 3616-56-6 ]
  • [ 57-14-7 ]
  • [ 29314-43-0 ]
  • 20
  • [ 3616-56-6 ]
  • [ 504-63-2 ]
  • [ 4740-66-3 ]
  • 21
  • [ 3616-56-6 ]
  • [ 1068-57-1 ]
  • N-acetyl-N-(dimethylaminoethyl)hydrazine dihydrochloride [ No CAS ]
  • 22
  • [ 6117-80-2 ]
  • [ 3616-56-6 ]
  • 2-(N,N-dimethyl)-4,7-dihydro-1,3-dioxepin [ No CAS ]
  • 23
  • [ 3616-56-6 ]
  • [ 27393-85-7 ]
  • [ 111296-91-4 ]
YieldReaction ConditionsOperation in experiment
67% With acetic acid; at 118℃; for 8h;Inert atmosphere; Under a nitrogen atmosphere, 14.1 g (0.061 mol) of the intermediate A, 11.4 g (0.071 mol) ofN,N'-<strong>[3616-56-6]dimethylaminoacetaldehyde diethyl acetal</strong>, and 110.0 g of acetic acid were stirred for 8 hours while being heated at 118°C to reflux. After the reaction solution was cooled to room temperature, the precipitated crystal was collected by filtration and washed with acetic acid (30 ml) . The resultant crystal was subjected to purification by reslurrying to afford 10.4 g (67percent yield) of IC-2 as a white crystal.
67% With acetic acid; at 118℃; for 8h;Inert atmosphere; Under a nitrogen atmosphere, 14.1 g (0.061 mol) of Intermediate C, 11.4 g (0.071 mol) of N,N?-<strong>[3616-56-6]dimethylaminoacetaldehyde diethyl acetal</strong>, and 110.0 g of acetic acid were stirred for 8 hr while being refluxed under heat at 118° C. After the reaction solution had been cooled to room temperature, the precipitated crystal was taken by filtration and washed with acetic acid (30 ml). The resultant crystal was subjected to re-slurry purification to provide 10.4 g (0.041 mol, yield: 67percent) of 5,12-dihydroindolo[3,2-a]carbazole (IC-5) as a white crystal.
60% With acetic acid; at 130℃;Inert atmosphere; (3) 1H,1'H-2,3'-biindole (16.4 g, 70.6 mmol) and 2,2-diethoxy-N,N-dimethylethanamine (14.18 ml, 78 mmol) in glacial acetic acid (160 mL) were refluxed at 130 °C overnight under nitrogen. The reaction solution was cooled to room temperature and filtered. The filtrate was washed with small amount of acetic acid and excess of water. The filtrate was dried in the oven at 65°C overnight affording 10.79 g (60percent) of the 5,12-dihydroindolo[3,2-a]carbazole as gray solid.
  • 25
  • dimethyl-propyl-acetalyl-ammonium hydroxide [ No CAS ]
  • [ 3616-56-6 ]
  • 26
  • [ 3616-56-6 ]
  • 5-amino-1,8,13-triaza-benzo[<i>fg</i>]naphthacen-9-one [ No CAS ]
  • 5-(2-dimethylamino-ethylamino)-1,8,13-triaza-benzo[<i>fg</i>]naphthacen-9-one [ No CAS ]
  • 27
  • [ 3616-56-6 ]
  • [ 71-43-2 ]
  • [ 7647-54-3 ]
  • 28
  • [ 3616-56-6 ]
  • [ 615552-57-3 ]
  • [ 139083-26-4 ]
YieldReaction ConditionsOperation in experiment
61% With acetic acid; at 100℃; for 1h; General procedure: Dimethylaminoacetaldehyde diethyl acetal (5 mmol) was added to a solution of 7 (0.5 mmol) in AcOH (5mL) at room temperature, and the mixture was heated at 100 °C. After 1 h, the mixture was gradually cooled to room temperature. The mixture was diluted with AcOEt (100 mL), washed with saturated NaHCO3 solution and brine, and dried over MgSO4. The solvent was removed, and the residue was separated by silica gel column chromatography with hexane/AcOEt (5:1) to give 3, 4 and 8.
  • 29
  • [ 3616-56-6 ]
  • [ 615552-51-7 ]
  • 3-methoxy-11-methyl-11,12-dihydro-11,12-diaza-indeno[2,1-<i>a</i>]fluorene [ No CAS ]
  • 30
  • [ 3616-56-6 ]
  • [ 615552-60-8 ]
  • [ 139083-25-3 ]
YieldReaction ConditionsOperation in experiment
65% With acetic acid; at 100℃; for 2h; The mixture of homocoupling product 2i (0.5 mmol), NaOEt (340.25 mg, 5.0 mmol) and DMSO (1.0 mL) was added into a 35 ml pressure-resistant vial under air atmosphere. The mixture was heated to 120oC and stirred for 5h. After being cooled to ambient temperature, the reaction mixture was diluted with EtOAc (60 mL) and washed with H2O (2×30 mL). The aqueous phase was extracted with EtOAc (2×30 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated under the reduced pressure. The residue was purified by silica gel column directly to give the product 3i (Yield 82%). The spectra of 3i were in accordance with those reported in the literature3. Then 16.1mg (1.0 mmol) (dimethylamino)acetaldehyde diethyl acetal was added in the refluxing mixture of 30 mg (0.10 mmol) biindole 3i with the 3ml of AcOH solvent. The resulting mixture was refluxed for 2 h, then cooled to room temperature, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give tjipanazole D (4i) with 65% yield (21.1 mg). The spectra of 4i were in accordance with those reported in the literature3,4,5.
60% With acetic acid; at 100℃; for 1h; General procedure: Dimethylaminoacetaldehyde diethyl acetal (5 mmol) was added to a solution of 7 (0.5 mmol) in AcOH (5mL) at room temperature, and the mixture was heated at 100 C. After 1 h, the mixture was gradually cooled to room temperature. The mixture was diluted with AcOEt (100 mL), washed with saturated NaHCO3 solution and brine, and dried over MgSO4. The solvent was removed, and the residue was separated by silica gel column chromatography with hexane/AcOEt (5:1) to give 3, 4 and 8.
  • 31
  • [ 3616-56-6 ]
  • [ 780759-85-5 ]
  • [ 780759-86-6 ]
  • 35
  • [ 1040411-48-0 ]
  • [ 3616-56-6 ]
  • [ 76-05-1 ]
  • C2HF3O2*C28H40ClFN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% Step 8B: Compound 8-2; To a flask containing (R)-1-{4-[2-((S)-l-amino-2-methyl-propyl)-6-fluoro-phenyl]- piperazin-l-yl}-3- (4-chloro-phenyl)-2-methyl-propan-l-one (43 mg, 0. 10 mmol) and (2,2- diethoxy-ethyl) -dimethyl-amine (100 pL, 0.50 mmol), TFA (30011L, 4.0 mmol) was added via syringe. After-5 min. , NaCNBH3 (95 mg, 1.5 mmol) was added and the resulting mixture was heated to 120 °C overnight. The resulting brown reaction mixture was concentrated in vacuo and purified via preparative HPLC/MS to furnish 8-2 (3.8 mg, 0.006 mmol, 6percent) as the TFA salt. LCMS-tR (method 4) 1.596 min. m/z 502.8 (M+ + H+).
  • 36
  • [ 3616-56-6 ]
  • [ 7732-18-5 ]
  • [ 94636-44-9 ]
  • N,N-Diethyl-5-[[2-(dimethylamino)ethyl]amino]-2H-[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine [ No CAS ]
  • N-[2-[2-(diethylamino)ethyl]-2H[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]-1,3-propanediamine, hydrochloride salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; toluene-4-sulfonic acid; In isopropyl alcohol; EXAMPLE 43 N,N-Diethyl-5-[[2-(dimethylamino)ethyl]amino]-2H-[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine A mixture of 5.0 g (0.015 mol) of 5-amino-N,N-diethyl-2H[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine, 2.4 g (0.015 mol) of 2,2-diethoxy-N,N-dimethyl ethanamine, and 0.001 g of p-toluenesulfonic acid in 100 ml of 2-propanol was heated under reflux for four hours, allowed to cool to room temperature, and treated portionwise with 1.0 g (0.026 mol) of NaBH4 over a two hour period. The mixture was stirred at room temperature for 16 hours and poured into 1 l of H2 O. The precipitate that formed was collected, washed with H2 O, dried, and recrystallized to give the product. An example of another 5-(monoalkylated or acylated)-2-(substituted)benzothiopyrano[4,3,2-cd]-indazole, prepared in the manner of Examples 5-11, is as follows: N-[2-[2-(diethylamino)ethyl]-2H[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]-1,3-propanediamine, hydrochloride salt, mp 222° C. dec.
  • 37
  • [ 7791-07-3 ]
  • [ 3616-56-6 ]
  • [ 42784-01-0 ]
YieldReaction ConditionsOperation in experiment
900 g (73.3%) With trichlorophosphate; In N-methyl-acetamide; hexane; chloroform; water; EXAMPLE 5 Preparation of N-(3-(dimethylamino)-2-ethoxy-2-propenylidene)-N-methylmethanaminium perchlorate A solution of 1293 g (17.7 mol) dimethylformamide and 1800 ml chloroform was cooled to 3° C. and 910 ml (9.76 mol) phosphorus oxychloride was added at the rate of 10 ml/minute. The resulting mixture was stirred for 30 minutes. N,N-Dimethylaminoacetaldehyde diethyl acetal, 727.9 g (4.51 mol), was added at the rate of 12-15 ml per minute, maintaining the temperature between 6° to 15° C. The mixture was heated at reflux for 31/2 hours, then allowed to stir overnight. The mixture was poured into 4800 g of ice and 3 l hexane and this mixture was agitated, and the organic phase separated and washed with 500 ml cold water. The combined aqueous phases were treated with 1091 g sodium perchlorate, monohydrate, and dissolved in 750 ml distilled water. Combination of the first and second crops gave 900 g (73.3percent) of N-(3-(dimethylamino)-2-ethoxy-2-propenylidene)-N-methylmethanaminium perchlorate, which could be purified by recrystallization from ethanol. M.p. 117°-120° C.
  • 38
  • [ 52333-90-1 ]
  • [ 52334-92-6 ]
  • [ 3616-56-6 ]
  • [ 52334-50-6 ]
YieldReaction ConditionsOperation in experiment
With sodium borohydrid; In ethanol; water; EXAMPLE 269 2-[3-(2-Dimethylaminoethyl)aminophenyl]oxazolo[4,5-b]pyridine A mixture of 1.1 g., (0.005 mole) of 2-(3-aminophenyl)oxazolo[4,5-b]pyridine and 50 ml. of ethanol is reacted with dimethylaminoacetaldehyde [from 0.96 g. (0.006 mole) dimethylaminoacetaldehyde diethylacetal]by gentle heating to complete the intermediate Schiff base formation. The mixture is then cooled and 60 mg., (0.0015 mole) of sodium borohydride is added, and the mixture allowed to stir overnight at room temperature. Water is added, the solvents are removed in vacuo, and the residue is distributed between water and methylene chloride. The organic layer is dried and concentrated in vacuo to give crude 2-[3-(2-dimethylaminoethyl)aminophenyl]oxazolo[4,5-b]pyridine, purified via column chromatography using an alumina column with an ethylacetate-ether mixture (v/v 0-60percent ethylacetate) as eluant.
  • 39
  • [ 3616-56-6 ]
  • ((trans,trans)-1-(2-(dimethylamino)ethyl)-4-(3-fluoro-2-methylphenyl)-5-((S)-2-(trifluoromethyl)pyrrolidine-1-carbonyl)piperidin-3-yl)(3-hydroxyphenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% A solution of the higher running product of (trans,trans)-tert-butyl 4-(3-fluoro-2- methylphenyl)-3-(3-hydroxybenzoyl)-5-((S)-2-(trifluoromethyl)pyrrolidine-l- carbonyl)piperidine-l-carboxylate (29 mg, 0.050 mmol) in THF (0.5 mL) was treated with HCl/dioxane solution (4 M, 5 mL) at room temperature and the mixture stirred overnight. The solvents were evaporated and the residue partitioned between EtOAc and saturated NaHCO3. The layers were separated and the organic phase was extracted with EtOAc. The combined organic layers were combined, dried over Na2SO4, and concentrated under vacuum to give 24 mg of a glassy solid, hi a separate flask, (dimethylamino)acetaldehyde diethyl acetal (1 g) was dissolved in 4 M HCl/dioxane solution (50 mL). Water (15 mL) was added and the resulting mixture stirred at 60 C for 30 min. The organic solvent was removed under vacuum and the pH of the remaining aqueous phase was adjusted with 1 M KOH to pH15. The mixture was extracted with dichloromethane, dried over Na2SO4, and concentrated under vacuum until -20 mL remained. The piperidine (24 mg) from above was treated with 1 mL of the above aldehyde/dichloromethane solution followed by NaBH(OAc)3 (75 mg, excess) in dichloromethane (3 mL). After stirring 30 min at room temperature, the reaction was quenched with NaHCpsi3 and the layers separated. The organic phase was washed with NaHCpsi3, dried over Na2SO4 and evaporated to dryness. The residue was purified over silica gel using 10percent <n="105"/>MeOH/dichloromethane to give pure desired ((trans, trans)- l-(2-(dimethylamino)ethyl)-4-(3- fluoro-2-methylphenyl)-5-((S)-2-(trifluoromethyl)pyrrolidine-l-carbonyl)piperidin-3-yl)(3- hydroxyphenyl)methanone (11 mg, 40percent yield) (characterized by LCMS and 1H NMR, LRMS (M+H+) m/z = 550.2.
  • 40
  • [ 3616-56-6 ]
  • [ 1413945-87-5 ]
YieldReaction ConditionsOperation in experiment
89.6% 40 g of dimethylaminoacetaldehyde diethylacetal are heated to 400C in a mixture of 48 g cone, hydrochloric acid and 20 ml of water for 3 h. Then a solution of 42.4 g sodium pyrosulphite in 72 ml of water (sodium hydrogen sulphite solution) is added dropwise and the mixture is stirred for 1 h. 200 ml of ethanol are added and then the mixture is stirred for 2 h at 00C. The suspension is suction filtered, washed with 160 ml of ethanol and dried at 45C in vacuo. Yield: 42.5 g (89.6 percent of theoretical) decomp.: from 180C
  • 41
  • [ 721449-93-0 ]
  • [ 3616-56-6 ]
  • [ 721450-94-8 ]
YieldReaction ConditionsOperation in experiment
0.027 g (20%) With sodium cyanoborohydride; In water; acetic acid; EXAMPLE 64 {2-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl-amine To a stirring solution of 2-chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamine (0.121 g, 0.386 mmol), (dimethylamino)acetaldehyde diethyl acetal (0.720 mL, 3.94 mmol), glacial acetic acid (24.0 mL) and water (0.100 mL, 5.55 mmol) was added sodium cyanoborohydride (0.140 g, 2.22 mmol). The solution was heated at 60° C. for 5 days and then the solution was stirred at room temperature until a precipitate formed. The suspension was filtered, the filter cake was washed with EtOAc (10 mL) and then the filtrate was concentrated by rotary evaporation. The residue was purified by flash column chromatography (silica gel, elution with EtOAc:hexanes, 1:3.5), gave 0.027 g (20percent) of the title compound as a white solid. 1H NMR (CDCl3): 7.60 (d, 1H, J=5.2 Hz), 7.44-7.35 (m, 3H), 7.13 (d, 1H, J=5.2 Hz), 4.33 (br s, 1H), 3.37-3.28 (m, 2H), 1.36 (t, 3H, J=7.1 Hz).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 3616-56-6 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 645-36-3

A544100 [645-36-3]

2,2-Diethoxyethanamine

Similarity: 0.80

Chemical Structure| 22483-09-6

A727306 [22483-09-6]

2,2-Dimethoxyethanamine

Similarity: 0.72

Chemical Structure| 70384-51-9

A980432 [70384-51-9]

Tris(2-(2-methoxyethoxy)ethyl)amine

Similarity: 0.67

Chemical Structure| 25408-61-1

A106468 [25408-61-1]

2,2-Dimethoxy-N,N-dimethylacetamide

Similarity: 0.64

Chemical Structure| 62005-48-5

A526334 [62005-48-5]

N-(2,2-Dimethoxyethyl)acetamide

Similarity: 0.64

Ethers

Chemical Structure| 3616-59-9

A183658 [3616-59-9]

4-(2,2-Diethoxyethyl)morpholine

Similarity: 0.93

Chemical Structure| 22633-57-4

A448433 [22633-57-4]

4-(2,2-Dimethoxyethyl)morpholine

Similarity: 0.89

Chemical Structure| 645-36-3

A544100 [645-36-3]

2,2-Diethoxyethanamine

Similarity: 0.80

Chemical Structure| 3616-58-8

A553994 [3616-58-8]

1-(2,2-Diethoxyethyl)piperidine

Similarity: 0.76

Chemical Structure| 22483-09-6

A727306 [22483-09-6]

2,2-Dimethoxyethanamine

Similarity: 0.72

Amines

Chemical Structure| 645-36-3

A544100 [645-36-3]

2,2-Diethoxyethanamine

Similarity: 0.80

Chemical Structure| 22483-09-6

A727306 [22483-09-6]

2,2-Dimethoxyethanamine

Similarity: 0.72

Chemical Structure| 70384-51-9

A980432 [70384-51-9]

Tris(2-(2-methoxyethoxy)ethyl)amine

Similarity: 0.67

Chemical Structure| 25408-61-1

A106468 [25408-61-1]

2,2-Dimethoxy-N,N-dimethylacetamide

Similarity: 0.64

Chemical Structure| 62005-48-5

A526334 [62005-48-5]

N-(2,2-Dimethoxyethyl)acetamide

Similarity: 0.64