Home Cart Sign in  
Chemical Structure| 144186-11-8 Chemical Structure| 144186-11-8

Structure of 144186-11-8

Chemical Structure| 144186-11-8

*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 [ 144186-11-8 ]

CAS No. :144186-11-8
Formula : C12H16N2O4
M.W : 252.27
SMILES Code : O=C(OC)C1=CN=C(NC(OC(C)(C)C)=O)C=C1
MDL No. :MFCD05663797
InChI Key :KHMRKCRGUHPQLA-UHFFFAOYSA-N
Pubchem ID :2764194

Safety of [ 144186-11-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 144186-11-8 ]

* 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 [ 144186-11-8 ]

[ 144186-11-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 79-37-8 ]
  • [ 144186-11-8 ]
  • [ 199296-40-7 ]
YieldReaction ConditionsOperation in experiment
With diisobutylaluminium hydride; triethylamine; In hexane; dichloromethane; water; dimethyl sulfoxide; Step B 2-(t-Butoxycarbonylamino)-5-pyridinecarboxaldehyde To a solution of methyl-6-(tert-butoxycarbonylamino)-nicotinate (2.20 g, 8.72 mmol) in anhydrous THF (50 mL), cooled to -30 C. was added DIBAL-H (1.0M in hexane, 34. 8 mL, 34.8 mmol) dropwise. After 1 h, 40 mL of a saturated solution of Rochelle salts was added and stirred vigorously for 10 h. The volatiles were removed in vacuo and the aqueous layer was extracted with methylene chloride (3*50 mL). The organic layer was washed with water (1*50 mL) and brine (1*50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was used directly in the next step. To a solution of oxalyl chloride (4.12 g, 32.46 mmol) in methylene chloride (30 mL), cooled to -78 C., was added DMSO (2.54 g, 32.46 mmol) dissolved in methylene chloride (9 mL) dropwise. After 20 minutes, the crude alcohol (1.82 g, 8.11 mmol) dissolved in 35 mL of methylene chloride was added followed by triethylamine (4.92 g, 48.66 mmoL). The ice bath was removed and the reaction stirred for 1 hr at rt, then water (30 mL) was added. The layers were separated and the aqueous layer was extracted with methylene chloride (2*50 mL). The organic layer was washed with water (1*50 mL) and brine (1*50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (30*150 mm column of SiO2, EtOAc/methylene chloride 1:11) to give the title compound as a colorless solid: 1 H NMR (400 MHz, CDCl3) d 1.55 (s, 9H), 7.79 (br s, 1H), 8.13-8.14 (m, 2H), 8.71 (dd, J=1.1 and 1.8 Hz, 1H), 9.96 (s, 1H).
With diisobutylaluminium hydride; triethylamine; In hexane; dichloromethane; water; dimethyl sulfoxide; Step B: 2-(t-Butoxycarbonylamino)-5-pyridinecarboxaldehyde To a solution of methyl-6-(tert-butoxycarbonylamino)-nicotinate (2.20 g, 8.72 mmol) in anhydrous THF (50 mL), cooled to -30C was added DIBAL-H (1.0M in hexane, 34.8 mL, 34.8 mmol) dropwise. After 1 h, 40 mL of a saturated solution of Rochelle salts was added and stirred vigorously for 10 h. The volatiles were removed in vacuo and the aqueous layer was extracted with methylene chloride (3 x 50 mL). The organic layer was washed with water (1 x 50 mL) and brine (1 x 50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was used directly in the next step. To a solution of oxalyl chloride (4.12 g, 32.46 mmol) in methylene chloride (30 mL), cooled to -78 C, was added DMSO (2.54 g, 32.46 mmol) dissolved in methylene chloride (9 mL) dropwise. After 20 minutes, the crude alcohol (1.82 g, 8.11 mmol) dissolved in 35 mL of methylene chloride was added followed by triethylamine (4.92 g, 48.66 mmoL). The ice bath was removed and the reaction stirred for 1 hr at rt, then water (30 mL) was added. The layers were separated and the aqueous layer was extracted with methylene chloride (2 x 50 mL). The organic layer was washed with water (1 x 50 mL) and brine (1 x 50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (30 x 150 mm column of SiO2, EtOAc/methylene chloride 1:11) to give the title compound as a colorless solid: 1H NMR (400 MHz, CDCl3) d 1.55 (s, 9H), 7.79 (br s, 1H), 8.13-8.14 (m, 2H), 8.71 (dd, J = 1.1 and 1.8 Hz, 1H), 9.96 (s, 1H).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 144186-11-8 ]

Amides

Chemical Structure| 169280-82-4

A325514 [169280-82-4]

Ethyl 6-((tert-butoxycarbonyl)amino)nicotinate

Similarity: 0.99

Chemical Structure| 231958-14-8

A243598 [231958-14-8]

6-((tert-Butoxycarbonyl)amino)nicotinic acid

Similarity: 0.99

Chemical Structure| 365413-11-2

A588604 [365413-11-2]

6-((tert-Butoxycarbonyl)(methyl)amino)nicotinic acid

Similarity: 0.94

Chemical Structure| 934373-39-4

A862994 [934373-39-4]

2-((tert-Butoxycarbonyl)amino)nicotinic acid

Similarity: 0.94

Chemical Structure| 639091-75-1

A234239 [639091-75-1]

Methyl 2-((tert-butoxycarbonyl)amino)isonicotinate

Similarity: 0.94

Esters

Chemical Structure| 169280-82-4

A325514 [169280-82-4]

Ethyl 6-((tert-butoxycarbonyl)amino)nicotinate

Similarity: 0.99

Chemical Structure| 639091-75-1

A234239 [639091-75-1]

Methyl 2-((tert-butoxycarbonyl)amino)isonicotinate

Similarity: 0.94

Amines

Chemical Structure| 169280-82-4

A325514 [169280-82-4]

Ethyl 6-((tert-butoxycarbonyl)amino)nicotinate

Similarity: 0.99

Chemical Structure| 231958-14-8

A243598 [231958-14-8]

6-((tert-Butoxycarbonyl)amino)nicotinic acid

Similarity: 0.99

Chemical Structure| 365413-11-2

A588604 [365413-11-2]

6-((tert-Butoxycarbonyl)(methyl)amino)nicotinic acid

Similarity: 0.94

Chemical Structure| 934373-39-4

A862994 [934373-39-4]

2-((tert-Butoxycarbonyl)amino)nicotinic acid

Similarity: 0.94

Chemical Structure| 639091-75-1

A234239 [639091-75-1]

Methyl 2-((tert-butoxycarbonyl)amino)isonicotinate

Similarity: 0.94

Related Parent Nucleus of
[ 144186-11-8 ]

Pyridines

Chemical Structure| 169280-82-4

A325514 [169280-82-4]

Ethyl 6-((tert-butoxycarbonyl)amino)nicotinate

Similarity: 0.99

Chemical Structure| 231958-14-8

A243598 [231958-14-8]

6-((tert-Butoxycarbonyl)amino)nicotinic acid

Similarity: 0.99

Chemical Structure| 365413-11-2

A588604 [365413-11-2]

6-((tert-Butoxycarbonyl)(methyl)amino)nicotinic acid

Similarity: 0.94

Chemical Structure| 934373-39-4

A862994 [934373-39-4]

2-((tert-Butoxycarbonyl)amino)nicotinic acid

Similarity: 0.94

Chemical Structure| 639091-75-1

A234239 [639091-75-1]

Methyl 2-((tert-butoxycarbonyl)amino)isonicotinate

Similarity: 0.94