Home Cart 0 Sign in  

[ CAS No. 6011-14-9 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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
Excepted Quantity Free
Inaccessible (Haz class 6.1), Domestic USD 41.00
Inaccessible (Haz class 6.1), International USD 64.00
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 83.00
Accessible (Haz class 3, 4, 5 or 8), International USD 133.00
Chemical Structure| 6011-14-9
Chemical Structure| 6011-14-9
Structure of 6011-14-9 * Storage: {[proInfo.prStorage]}

Quality Control of [ 6011-14-9 ]

Related Doc. of [ 6011-14-9 ]

SDS
Alternatived Products of [ 6011-14-9 ]
Alternatived Products of [ 6011-14-9 ]

Product Details of [ 6011-14-9 ]

CAS No. :6011-14-9 MDL No. :MFCD00012850
Formula : C2H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :92.53 g/mol Pubchem ID :11491918
Synonyms :

Safety of [ 6011-14-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P405-P501 UN#:3439
Hazard Statements:H301-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6011-14-9 ]

  • Upstream synthesis route of [ 6011-14-9 ]
  • Downstream synthetic route of [ 6011-14-9 ]

[ 6011-14-9 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 131543-46-9 ]
  • [ 6011-14-9 ]
  • [ 6270-63-9 ]
Reference: [1] Patent: US2805223, 1955, ,
  • 2
  • [ 17280-41-0 ]
  • [ 6011-14-9 ]
  • [ 5521-58-4 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 51, p. 9287 - 9290
  • 3
  • [ 6011-14-9 ]
  • [ 151169-75-4 ]
  • [ 3218-49-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 4
  • [ 16419-60-6 ]
  • [ 6011-14-9 ]
  • [ 22364-68-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 5
  • [ 128796-39-4 ]
  • [ 6011-14-9 ]
  • [ 2338-75-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 6
  • [ 1679-18-1 ]
  • [ 6011-14-9 ]
  • [ 140-53-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 7
  • [ 5122-99-6 ]
  • [ 6011-14-9 ]
  • [ 51628-12-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 8
  • [ 6011-14-9 ]
  • [ 67492-50-6 ]
  • [ 52516-37-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 9
  • [ 1013-88-3 ]
  • [ 6011-14-9 ]
  • [ 70591-20-7 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 13, p. 2663 - 2666
[2] Journal of the American Chemical Society, 1980, vol. 102, # 10, p. 3592 - 3600
[3] Patent: WO2005/28429, 2005, A2, . Location in patent: Page/Page column 61-62
[4] Patent: WO2006/60494, 2006, A1, . Location in patent: Page/Page column 49
[5] Patent: WO2006/60810, 2006, A1, . Location in patent: Page/Page column 72-73
[6] Patent: WO2008/42968, 2008, A2, . Location in patent: Page/Page column 34
[7] Patent: WO2005/74904, 2005, A2, . Location in patent: Page/Page column 63
[8] Patent: WO2010/56877, 2010, A2, . Location in patent: Page/Page column 51-52
[9] Patent: WO2006/34004, 2006, A2, . Location in patent: Page/Page column 62-63
[10] Patent: WO2009/123623, 2009, A1, . Location in patent: Page/Page column 38-39
[11] Patent: WO2006/102535, 2006, A2, . Location in patent: Page/Page column 58
[12] Patent: WO2008/42968, 2008, A2, . Location in patent: Page/Page column 34
[13] Patent: WO2005/74904, 2005, A2, . Location in patent: Page/Page column 63
  • 10
  • [ 119-61-9 ]
  • [ 6011-14-9 ]
  • [ 70591-20-7 ]
Reference: [1] Synthetic Communications, 1995, vol. 25, # 3, p. 369 - 378
[2] Synthetic Communications, 1999, vol. 29, # 9, p. 1561 - 1569
  • 11
  • [ 89598-96-9 ]
  • [ 6011-14-9 ]
  • [ 31938-07-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 12
  • [ 6011-14-9 ]
  • [ 99768-12-4 ]
  • [ 76469-88-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 13
  • [ 773837-37-9 ]
  • [ 50-00-0 ]
  • [ 6011-14-9 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 49, p. 6577 - 6580
  • 14
  • [ 6011-14-9 ]
  • [ 108-95-2 ]
  • [ 19745-72-3 ]
Reference: [1] Patent: CN105622438, 2016, A, . Location in patent: Paragraph 0030; 0031; 0032
  • 15
  • [ 6011-14-9 ]
  • [ 501-53-1 ]
  • [ 75-36-5 ]
  • [ 51030-44-5 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 46, p. 7459 - 7462
  • 16
  • [ 24424-99-5 ]
  • [ 6011-14-9 ]
  • [ 85363-04-8 ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydrogencarbonate In tetrahydrofuran; water at 25 - 30℃; To a solution of hydrochloride salt of amino acetonitrile (50 g 487 mmol) dissolved in water (250 ml) and tetrahydrofuran (250 ml) was added sodium bicarbonate (90.14 g, 1073 mmol) under stirring at 25-30 °C. To this was added di- ie/t-butyldicarbonate (117 g, 536 mmol) drop-wise using addition funnel. The progress of reaction was monitored by thin layer chromatography using a mixture of hexane and acetone as solvent. After complete consumption of starting material, ethyl acetate (500 ml) was added to it and organic layer was separated. The aqueous layer was re-extracted with ethyl acetate (1x250 ml). The organic extracts were combined and dried over anhydrous sodium sulfate, then concentrated to yield 66 g of tert-butyl (cyanomethyl)carbamate as a thick liquid in 86percent yield
66% With triethylamine In dichloromethane for 16 h; Reflux Step a:
Aminoacetonitrile hydrochloride (5 g, 54 mmol) was added to dichloromethane (30 mL).
A solution of di-tert-butyl dicarbonate (11.9 g, 54.6 mmol, 1.01 equiv.) and TEA (24.6 g, 33.7 mL, 243 mmol, 4.5 equiv.) in dichloromethane (25 mL) was also metered in.
After completion of the addition the mixture was heated for 16 h under reflux.
After the reaction mixture had cooled it was filtered, the filtrate was washed with water (50 mL), dried over magnesium sulphate and freed from solvent under reduced pressure. N-boc-aminoacetonitrile (5.58 g, 66percent yield) remained as a brownish oil, which was used without further purification.
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 10, p. 1845 - 1895
[2] Synthetic Communications, 1994, vol. 24, # 12, p. 1767 - 1772
[3] Tetrahedron, 1988, vol. 44, # 18, p. 5833 - 5844
[4] Helvetica Chimica Acta, 1986, vol. 69, p. 1224 - 1262
[5] Patent: WO2017/81615, 2017, A1, . Location in patent: Page/Page column 33
[6] Acta Crystallographica Section C: Crystal Structure Communications, 1997, vol. 53, # 7, p. 959 - 961
[7] Patent: US2012/46301, 2012, A1, . Location in patent: Page/Page column 37
[8] Journal of Organic Chemistry, 1995, vol. 60, # 13, p. 4305 - 4308
[9] Patent: US5629152, 1997, A,
  • 17
  • [ 6011-14-9 ]
  • [ 188347-48-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 18
  • [ 14047-29-1 ]
  • [ 6011-14-9 ]
  • [ 1056636-11-3 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 40℃; for 3.5 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16 h;
To a suspension of 4-carboxyphenylboronic acid (5.0 g, 30 mmol) in DMF (5 mL) and dichloromethane (200 mL) at 0°C was added oxalylchloride (5.9 mL, 66 mmol) dropwise. <n="54"/>When gas evolution slowed, the ice bath was removed and the reaction allowed to warm to room temperature over 30 min. The reaction was then heated at 4O0C for 3 h by which time all solids had dissolved. The dichloromethane was removed by distillation and the DMF solution cooled to 00C. A solution of aminoacetonitrile hydrochloride (3.05 g, 33 mmol) in DMF (80 rnL) and DIPEA (13 mL, 75 mmol) was then added dropwise. After the addition was complete the ice bath was removed and the solution allowed to stir at room temperature for 16 h. Most of the DMF was then removed in vacuo and the reaction was partitioned between ethyl acetate and 2 M aqueous hydrochloric acid. The aqueous layer was extracted twice further with ethyl acetate and the combined organic fractions dried (Na2SO4) filtered and concentrated under reduced pressure to afford 4-(cyanomethylcarbamoyl)phenylboronic acid as a waxy pale yellow solid (5.34 g, 87percent). 1HNMR (J6-DMSO, 300 MHz) δ 9.18 (IH, br. t, J= 5.1Hz), 7.8-7.9 (4H, m), 4.31 (2H, d, J= 5.4 Hz). LC-MS: rt 0.9 min.; m/z 203.3 [M-H]".
87%
Stage #1: With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 40℃; for 3.5 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16 h;
Example 3 - Synthesis of Compound 90; To a suspension of 4-carboxyphenylboronic acid (5.0 g, 30 mmol) in DMF (5 mL) and dichloromethane (200 mL) at 0°C was added oxalylchloride (5.9 mL, 66 mmol) dropwise. When gas evolution slowed, the ice bath was removed and the reaction allowed to warm to room temperature over 30 min. The reaction was then heated at 400C for three hours by which time all solids had dissolved. The dichloromethane was removed by distillation and the DMF solution cooled to 0°C. A solution of aminoacetonitrile hydrochloride (3.05 g, 33 mmol) in DMF (80 mL) and DIPEA (13 mL, 75 mmol) was then added dropwise. After the addition was complete the ice bath was removed and the solution allowed to stir at room temperature for 16 h. Most of the DMF was then removed in vacuo and the reaction was partitioned between ethyl acetate and 2 M aqueous hydrochloric acid. The aqueous layer was extracted twice further with ethyl acetate and the combined organic fractions dried (Na2SO4) filtered and concentrated under reduced pressure to afford 4-(cyanomethylcarbamoyl)phenylboronic acid as a waxy pale yellow solid (5.34 g, 87percent). 1H NMR (300 MHz, J6-DMSO): 9.18 (br. t, J- 5.1Hz, IH), 7.8-7.9 (m, 4H), 4.31 (d, J= 5.4 Hz, 2H); LC-ESI-MS (method B): rt 0.9 min.; m/z 203.3 [M-H]-.
Reference: [1] Patent: WO2009/29998, 2009, A1, . Location in patent: Page/Page column 52-53
[2] Patent: WO2008/109943, 2008, A1, . Location in patent: Page/Page column 60
  • 19
  • [ 945749-71-3 ]
  • [ 6011-14-9 ]
  • [ 1056634-68-4 ]
YieldReaction ConditionsOperation in experiment
90% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Et3N (4.1 mL, 30 mmol) was added to a mixture of compound 6(1.88 g, 5.0 mmol) in DMF (20 mL). Then aminoacetonitrile hydrochloride (0.93 g, 10 mmol) was added followed by N-hydroxybenzotriazole (HOBt, 0.81 g, 6.0 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.1 g, 6.0 mmol). The mixture was stirred overnight at room temperature. After removing the solvents under reduced pressure, the residue was dissolved in CH2Cl2 (100 mL) and washed with NaHCO3 aqueous solution. The organic phase was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography on 200–300 mesh silica with EtOAc to afford momelotinib as: Yellow solid; yield 1.86 g (90percent); m.p. 232–234 °C (lit.14 238–243 °C); IR: 3365, 3282, 1660, 1596, 1576, 1512, 1456, 1232 cm–1. Anal. calcd for C23H22N6O2: C, 66.65; H, 5.35; N, 20.28; found: C, 66.78; H, 5.49; N, 20.39percent. ESI-MS: 415.1 [M + H]+, 437.1 [M + Na]+, 413.2 [M – H]–; 1H NMR (300 MHz, DMSO-d6): δ 9.47 (s, 1H), 9.32 (t, J = 5.4 Hz, 1H), 8.54 (d, J = 5.1 Hz, 1H), 8.27 (d,J = 8.1 Hz, 2H), 8.03 (d, J = 8.1 Hz, 2H), 7.67 (d, J = 8.7 Hz, 2H), 7.40 (d, J = 5.1 Hz, 1H), 6.94 (d, J = 8.7 Hz, 2H), 4.35 (d, J = 5.1 Hz, 2H), 3.74–3.77 (m, 4H), 3.04–3.07 (m, 4H); 13C NMR (75 MHz, DMSO-d6): δ 166.1, 162.4, 160.3, 159.2, 146.2, 139.9, 134.5, 132.8, 127.8, 126.9, 120.3, 117.5, 115.6, 107.6, 66.1, 49.2, 27.7.
90% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; To 2g (5.3mmol) C4 was added 4.42 ml (32mmol) triethylamine, 0.98g (10.6mmol) aminoacetonitrile hydrochloride, 1.22g (6.6mmol) EDCI, and 860 ml (6.6mmol) HOBT. It was dissolved in 20mL DMF. After reacting at room temperature overnight, concentrate to dry, by adding dichloromethane, with saturated sodium bicarbonate solution, salt water after washing, concentrating, methanol used for recrystallization to obtain the yellow solid, yield 90percent.
88% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide To a suspension of 4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)benzoic acid (theoretically 32.59 g, 86.6 mmol) in DMF (400 mL) was added triethylamine (72.4 mL, 519.6 mmol, 6 eq.) The mixture was sonicated to ensure dissolution. Aminoacetonitrile hydrochloride (16.02 g, 173.2 mmol) was added followed by iV-hydroxybenzotriazole (anhydrous, 14.04 g, 103.8 mmol) and l-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (19.92 g, 103.8 mmol). The suspension was stirred vigorously overnight. The solvent was evaporated under reduced pressure, the residue was diluted with 5percent sodium bicarbonate (400 mL) and water (300 mL), giving a yellow solid, which was broken up and filtered. The solids were washed several times with 100 mL portions of water, triturated with hot methanol/dichloromethane (500 mL, 1:1), concentrated to a volume of approximately 300 mL), cooled and filtered. The solids were washed with cold methanol (3 x 100 mL), ether (200 mL) and hexane (200 mL) prior to drying to afford Compound 3 (31.69 g, 88percent). M.p. 238-243°C. Microanalysis: Found C, 66.52; H, 5.41 ; N, 20.21. C23H26N6O10S2 requires C, 66.65; H, 5.35; N 20.28percent. 13C NMR (75.5MHz, J6-DMSO) δ 166.04, 162.34, 160.26, 159.14, 146.14, 139.87, 134.44, 132.73, 127.80, 126.84, 120.29, 117.49, 115.50, 107.51, 66.06, 49.16, 27.68.
24% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 20 h; Inert atmosphere 4-(2-(4-(morpholino)phenylamino) pyrimidin-4-yl) benzoic acid (0.500 g, 1.328 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.305 g, 1.594 mmol), 1-hydroxy-phenylpropyl triazole (0.215 g, 1.594 mmol), triethylamine (0.805 g, 7.968 mmol) and N,N-dimethylformamide (5 mL) were added to a flask under nitrogen protection. 2-amino-acetonitrile hydrochloride (0.368 g, 3.985 mmol) was added under stirring, and reacted for 20h under room temperature. Purified water (5mL) and saturated bicarbonate solution (5mL) were added to the reaction mixture, and there was yellow solid precipitated. After stirred for 30 mins, it was filtered and washed by clear water. The crude product was obtained after drying, and was separated and purified by preparative chromatography to obtain yellow solid desired product (0.130 g, PLC purity: 98.3percent, yield: 24percent); MS Calcd.: 414; MS Found: 415 (M+H)+; 1H NMR(400MHz, DMSO-d6) δ 9.63(1H, s), 9.38-9.35(1H, m), 8.57-8.56(1H, d), 8.29-8.27(2H, d), 8.05-8.03(2H, d), 7.74-7.71(2H, d), 7.46-7.44(1H, d), 7.07-7.05(2H, d), 4.37-4.36(2H, d), 3.80-3.78(4H, t), 3.15 ppm(4H, s).

Reference: [1] Journal of Chemical Research, 2016, vol. 40, # 8, p. 511 - 513
[2] Patent: , 2016, , . Location in patent: Paragraph 0049; 0050; 0051; 0052; 0053; 0054
[3] Patent: WO2008/109943, 2008, A1, . Location in patent: Page/Page column 58
[4] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2902 - 2905
[5] Patent: EP2949647, 2015, A1, . Location in patent: Paragraph 0124
Historical Records

Related Functional Groups of
[ 6011-14-9 ]

Nitriles

Chemical Structure| 25808-30-4

[ 25808-30-4 ]

2-(Methylamino)acetonitrile hydrochloride

Similarity: 0.75

Chemical Structure| 50846-36-1

[ 50846-36-1 ]

2-Amino-2-methylpropanenitrile hydrochloride

Similarity: 0.56

Amines

Chemical Structure| 25808-30-4

[ 25808-30-4 ]

2-(Methylamino)acetonitrile hydrochloride

Similarity: 0.75

Chemical Structure| 50846-36-1

[ 50846-36-1 ]

2-Amino-2-methylpropanenitrile hydrochloride

Similarity: 0.56

Chemical Structure| 624-60-2

[ 624-60-2 ]

N-Methylethanamine hydrochloride

Similarity: 0.55

Chemical Structure| 15572-56-2

[ 15572-56-2 ]

Propan-2-amine hydrochloride

Similarity: 0.55

Chemical Structure| 870-24-6

[ 870-24-6 ]

2-Chloroethanamine hydrochloride

Similarity: 0.50

Aliphatic Chain Hydrocarbons

Chemical Structure| 25808-30-4

[ 25808-30-4 ]

2-(Methylamino)acetonitrile hydrochloride

Similarity: 0.75

Chemical Structure| 50846-36-1

[ 50846-36-1 ]

2-Amino-2-methylpropanenitrile hydrochloride

Similarity: 0.56

Chemical Structure| 624-60-2

[ 624-60-2 ]

N-Methylethanamine hydrochloride

Similarity: 0.55

Chemical Structure| 15572-56-2

[ 15572-56-2 ]

Propan-2-amine hydrochloride

Similarity: 0.55

Chemical Structure| 870-24-6

[ 870-24-6 ]

2-Chloroethanamine hydrochloride

Similarity: 0.50