[ CAS No. 60295-11-6 ] {[proInfo.proName]}

Name: 60295-11-6|tert-Butyl 2-cyclohexylidenehydrazinecarboxylate|98%
Brand: Ambeed
SKU: A206607
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3d Animation Molecule Structure of 60295-11-6

Structure of 60295-11-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 60295-11-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 60295-11-6 ]

SDS Specification

Alternatived Products of [ 60295-11-6 ]

Product Details of [ 60295-11-6 ]

CAS No. :	60295-11-6	MDL No. :	MFCD00447802
Formula :	C₁₁H₂₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VBSQBVWEZOIWGF-UHFFFAOYSA-N
M.W :	212.29	Pubchem ID :	4235373
Synonyms :

Calculated chemistry of [ 60295-11-6 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	61.08
TPSA :	50.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.78
Log Po/w (XLOGP3) :	2.11
Log Po/w (WLOGP) :	2.83
Log Po/w (MLOGP) :	1.86
Log Po/w (SILICOS-IT) :	2.06
Consensus Log Po/w :	2.33

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.22
Solubility :	1.27 mg/ml ; 0.006 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.332 mg/ml ; 0.00157 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.54
Solubility :	0.614 mg/ml ; 0.00289 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.35

Safety of [ 60295-11-6 ]

Signal Word:	Danger	Class:	4.1
Precautionary Statements:	P240-P210-P264-P280-P370+P378-P337+P313	UN#:	1325
Hazard Statements:	H315-H319-H228	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 60295-11-6 ]

* 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.

Upstream synthesis route of [ 60295-11-6 ]
Downstream synthetic route of [ 60295-11-6 ]

[ 60295-11-6 ] Synthesis Path-Upstream 1~1

1
[ 60295-11-6 ]
[ 24214-73-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: With sodium cyanoborohydride In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; ethanol for 1 h; Heating / reflux	t-Butylcarboxycyclohexanone hydrazone generated above (40.02 g, 189 mmol) was dissolved in a mixture of 175 mL tetrahydrofuran and 225 mL anhydrous methanol. Sodium cyanoborohydride (Acros, 14.3 g, 227 mmol) was added in portions over ten minutes and the mixture was stirred under argon overnight at room temperature. 135 mL of 6N hydrochloric acid were then added dropwise and the mixture was refluxed for one hour. The reaction was permitted to cool to room temperature and a white solid was removed by filtration. The mother liquor was concentrated and residual water was removed by azeotroping with ethanol on a rotary evaporator (3.x.100 mL). The mixture was concentrated to dryness and was taken up into hot isopropanol (300 mL). The solid that was present was removed by filtration and the mother liquor was concentrated to 1/2 volume at which point an equal volume of ethyl ether was added. This caused cyclohexylhydrazine hydrochloride to precipitate as a white solid. Yield (20.0 g, 93percent).

Reference： [1] Patent: US2007/281949, 2007, A1, . Location in patent: Page/Page column 17
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 2, p. 393 - 404
[3] Journal of Organic Chemistry, 1981, vol. 46, # 26, p. 5413 - 5414
[4] Patent: WO2016/123392, 2016, A2,

[ 60295-11-6 ] Synthesis Path-Downstream 1~1

1
[ 60295-11-6 ]
[ 60295-21-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium 10% on activated carbon; hydrogen In methanol at 50℃;	20.B Step B: tert-butyl 2-cyclohexyihydrazinecarboxylate To a stirred solution of tert-butyl 2-cyclohexylidenehydrazinecarboxylate (5.6 g, 1.0 eq) in 100 mL MeOH was added Pd/C (0.6 g, 10%). After addition was completed, the reaction was stirred at 50 °C overnight under H2 (10 atm) atmosphere. The mixture was filtered through a celite and the filtrate was concentrated to give the product (5.1 g, 92%) as a white solid. ‘H NMR (400 MHz, CDC13) ö 6.05 (s, 1H), 3.89 (brs, 1H), 2.76-2.81 (m, 1H), 1.81-1.84 (m, 2H), 1.71-1.75(m, 2H), 1.58-1.62(m, 1H), 1.46(s, 9H), 1.08-1.28(5H, m).
71.95%	With sodium tetrahydroborate In methanol at 50℃; for 8.33333h; Heating / reflux;	1.1 EXAMPLE-1; 3-[1-Oxo-2-(-(1-cyclohexyl)hydrazino)]ethyl-4-cyano thiazolidine trifluoroacetate [Compound No. 21); Step: 1 A solution of tert-butyl cyclohexylidine (8.0 g, 37.7 mmol) in methanol (50 ml) was warmed to 50° C. and then added sodium borohydride (11.4 g, 301.6 mmol) in portions over a period of 20 minutes. Refluxed for 8 hrs. Reaction mixture is concentrated in vacuo. Reaction mixture diluted with water and extracted with ethylacetate. Ethylacetate layer washed with water, dried (Na2 SO4), evaporated to dryness yielding the crude mass which is purified by column chromatography (5% ethyl acetate/hexane) gives N-cyclohexyl tert-butyl carbazate. (Yield 5.81 g, 71.95%).
71.95%	With sodium tetrahydroborate In methanol at 50℃; for 8h; Heating / reflux;	1.1 EXAMPLE-1 3-[1-Oxo-2-(-(1-cyclohexyl)hydrazino)]ethyl-4-cyano Thiazolidine Trifluoroacetate [Compound No.21). EXAMPLE-1 3-[1-Oxo-2-(-(1-cyclohexyl)hydrazino)]ethyl-4-cyano Thiazolidine Trifluoroacetate [Compound No.21). [0520] Step: 1 [0521] A solution of tert-butyl cyclohexylidine (8.0 g, 37.7 mmol) in methanol (50 ml) was warmed to 50° C. and then added sodium borohydride (11.4 g, 301.6 mmol) in portions over a period of 20 minutes. Refluxed for 8 hrs. Reaction mixture is concentrated in vacuo. Reaction mixture diluted with water and extracted with ethylacetate. Ethylacetate layer washed with water, dried (Na2 SO4), evaporated to dryness yielding the crude mass which is purified by column chromatography (5% ethyl acetate/hexane) gives N-cyclohexyl tert-butyl carbazate. (Yield 5.81 g, 71.95%).

58%	With sodium tetrahydroborate In tetrahydrofuran; methanol Reflux;	161.2 Example 161: 4-chloro-N-(4-chlorophenyl)-1-cyclohexyl-3-methyl-1H-pyrazolo [3,4-b]pyridine-5-carboxamide General procedure: To a solution of tert-butyl 2-cyclohexylidenehydrazine-1-carboxylate (crode, 15.1 mmol) in THF/MeOH (1/1, 50 mL) was added NaBH4 (2.8 g, 75.5 mmol), it was then refluxed overnight. Resultant was evaporated to remove solvent, then residue was diluted with EA (100 mL) and quenched by water (100 mL), organic layer was concentrated to afford 1.9 g (yield: 58%) of tert-butyl 2-cyclohexylhydrazine-1-carboxylate as colorless oil.‘HNMR (300 MHz, DMSO-d6): = 8.15 (s, 1H), 4.11 (s, 1H), 2.65-2.58 (m, 1H), 1.70-1.66 (m, 5H), 1.41 (s, 9H), 1.19-0.93 (m, 5H);
	With hydrogen In ethanol
	With borane-THF In tetrahydrofuran for 0.166667h; Ambient temperature;
	With borane In tetrahydrofuran at 20℃; for 0.333333h;	177.A To a solution of cyclohexanone (1.25 mL) in hexanes (8 mL) was added 1.59 g of tert-butyl carbazate. The mixture was heated at reflux for 10 min and then allowed to cool to RT. The white precipitate that had formed was removed by filtration and washed with cold hexanes. The white solid was then treated with BH3 (1. 0 M in THF, 12 mL). After stirring at RT for 20 min, the mixture was treated with 16 mL of 6 N HCI. The mixture was heated at 110°C for 20 min and then was concentrated in vacuo. The residue was treated with 30 mL of THF. The title compound (1.82 g), a white solid, was collected from this mixture by filtration. MS (ESI) : exact mass calculated for C6H14N2, 114.12 ; found, mlz 115. 1 [M+H] +. 1H NMR (500 MHz, CDC13) : 3.05-2. 99 (m, 1H), 2.11-2. 09 (m, 2H), 1.88-1. 86 (m, 2H), 1.72-1. 69 (m, 1H), 1.37-1. 19 (m, 5H).
	Stage #1: tert-butyl 2-cyclohexylidenehydrazine-1-carboxylate With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 16h; Stage #2: With sodium hydroxide; water In methanol at 0℃;	The intermediate imine was dissolved in MeOH (30 mL) and sodium cyanoborohydride (ALDRICH, 45.9 mmol) and glacial acetic acid (8.2 mL, 143.2 mmol) were added. After stirring the resulting reaction mixture at room temperature for 16h, it was cooled down to 0 °C and neutralised with 2N aq. NaOH (8.2 mL). The organic solvent was evaporated under vacuum and product was extracted with DCM. The combined organic layers were washed with brine and dried over anhydrous Na2SO4, yielding the above title compound. 1H NMR (300 MHz, CDCl3) δ ppm: 2.90- 2.76 (m, 1H), 1.94- 1.8 (m, 2H), 1.79- 1.7 (m, 2H), 1.67- 1.57 (m, 1H), 1.54- 1.42 (br., 9H), 1.40- 1.02 (br. m, 6H).
	With borane-THF In tetrahydrofuran at 40 - 60℃; for 1h;

Reference： [1]Current Patent Assignee: SHOUYAO HOLDINGS BEIJING CO LTD - WO2014/82598, 2014, A1 Location in patent: Paragraph 0418
[2]Current Patent Assignee: TORRENT INVESTMENTS PRIVATE LIMITED - US2003/225102, 2003, A1 Location in patent: Page 25
[3]Current Patent Assignee: TORRENT INVESTMENTS PRIVATE LIMITED - US2004/106802, 2004, A1 Location in patent: Page 33
[4]Current Patent Assignee: SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE - WO2016/123392, 2016, A2 Location in patent: Paragraph 00475
[5]Baumgarten,H.E. et al. [Journal of Organic Chemistry, 1976, vol. 41, p. 3805 - 3811]
[6]Ghali, N. I.; Venton, D. L.; Hung, S. C.; Le Breton, G. C. [Journal of Organic Chemistry, 1981, vol. 46, # 26, p. 5413 - 5414]
[7]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2005/40169, 2005, A2 Location in patent: Page/Page column 150
[8]Current Patent Assignee: GLAXOSMITHKLINE PLC - EP1918284, 2008, A1 Location in patent: Page/Page column 25
[9]Connolly, Terrence J.; Crittall, Andrew J.; Ebrahim, Alkarim S.; Ji, Guijun [Organic Process Research and Development, 2000, vol. 4, # 6, p. 526 - 529]

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P101	If medical advice is needed,have product container or label at hand.
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P234	Keep only in original container.
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P321
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P378
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
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P308 + P313	IF exposed or concerned: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H221	Flammable gas
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H240	Heating may cause an explosion
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H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H271	May cause fire or explosion; strong oxidizer
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Health hazards
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
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H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H336	May cause drowsiness or dizziness
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
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H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 60295-11-6 ] {[proInfo.proName]}

Quality Control of [ 60295-11-6 ]

Related Doc. of [ 60295-11-6 ]

Product Details of [ 60295-11-6 ]

Calculated chemistry of [ 60295-11-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 60295-11-6 ]

Application In Synthesis of [ 60295-11-6 ]

[ 60295-11-6 ] Synthesis Path-Upstream 1~1

[ 60295-11-6 ] Synthesis Path-Downstream 1~1

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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