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[ CAS No. 110-70-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 110-70-3
Chemical Structure| 110-70-3
Chemical Structure| 110-70-3
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Product Details of [ 110-70-3 ]

CAS No. :110-70-3 MDL No. :MFCD00008290
Formula : C4H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :KVKFRMCSXWQSNT-UHFFFAOYSA-N
M.W : 88.15 Pubchem ID :8070
Synonyms :

Calculated chemistry of [ 110-70-3 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 26.95
TPSA : 24.06 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : -0.62
Log Po/w (WLOGP) : -0.57
Log Po/w (MLOGP) : -0.18
Log Po/w (SILICOS-IT) : -0.36
Consensus Log Po/w : -0.03

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.2
Solubility : 140.0 mg/ml ; 1.59 mol/l
Class : Highly soluble
Log S (Ali) : 0.59
Solubility : 341.0 mg/ml ; 3.86 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.47
Solubility : 3.01 mg/ml ; 0.0342 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 110-70-3 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2734
Hazard Statements:H226-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 110-70-3 ]

* 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 [ 110-70-3 ]
  • Downstream synthetic route of [ 110-70-3 ]

[ 110-70-3 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 201230-82-2 ]
  • [ 110-70-3 ]
  • [ 80-73-9 ]
Reference: [1] Synthesis, 2010, # 24, p. 4251 - 4255
[2] Organic Letters, 1999, vol. 1, # 7, p. 961 - 964
  • 2
  • [ 124-38-9 ]
  • [ 110-70-3 ]
  • [ 80-73-9 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 6, p. 1567 - 1577
[2] Journal of Organic Chemistry, 1992, vol. 57, # 28, p. 7339 - 7342
[3] Chemical Communications, 2009, # 3, p. 349 - 351
  • 3
  • [ 124-38-9 ]
  • [ 109-73-9 ]
  • [ 110-70-3 ]
  • [ 80-73-9 ]
  • [ 1792-17-2 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 28, p. 7339 - 7342
  • 4
  • [ 124-38-9 ]
  • [ 109-73-9 ]
  • [ 110-70-3 ]
  • [ 80-73-9 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 28, p. 7339 - 7342
  • 5
  • [ 5852-49-3 ]
  • [ 110-70-3 ]
  • [ 80-73-9 ]
Reference: [1] Synthesis, 1983, # 12, p. 1032 - 1033
  • 6
  • [ 75-44-5 ]
  • [ 110-70-3 ]
  • [ 80-73-9 ]
Reference: [1] Journal of Molecular Structure, 1981, vol. 77, p. 239 - 252
  • 7
  • [ 75-44-5 ]
  • [ 110-70-3 ]
  • [ 80-73-9 ]
  • [ 117688-91-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 1, p. 228 - 236
  • 8
  • [ 20260-53-1 ]
  • [ 110-70-3 ]
  • [ 16837-38-0 ]
  • [ 72301-63-4 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 4, p. 629 - 632
  • 9
  • [ 50-99-7 ]
  • [ 74-89-5 ]
  • [ 6284-40-8 ]
  • [ 110-70-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 46, p. 14540 - 14544[2] Angew. Chem., 2017, vol. 129, p. 14732 - 14736,5
  • 10
  • [ 67-56-1 ]
  • [ 107-15-3 ]
  • [ 110-18-9 ]
  • [ 142-25-6 ]
  • [ 108-00-9 ]
  • [ 109-81-9 ]
  • [ 110-70-3 ]
Reference: [1] Patent: JP2005/41806, 2005, A, . Location in patent: Page/Page column 8
  • 11
  • [ 67-56-1 ]
  • [ 107-15-3 ]
  • [ 108-00-9 ]
  • [ 109-81-9 ]
  • [ 110-70-3 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 23, p. 7368 - 7377
  • 12
  • [ 67-56-1 ]
  • [ 107-15-3 ]
  • [ 110-18-9 ]
  • [ 142-25-6 ]
  • [ 108-00-9 ]
  • [ 109-81-9 ]
  • [ 110-70-3 ]
Reference: [1] Patent: JP2005/41806, 2005, A, . Location in patent: Page/Page column 8
  • 13
  • [ 106-93-4 ]
  • [ 74-89-5 ]
  • [ 106-58-1 ]
  • [ 105-84-0 ]
  • [ 105-78-2 ]
  • [ 110-70-3 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 38, p. 7565 - 7570
  • 14
  • [ 107-06-2 ]
  • [ 74-89-5 ]
  • [ 105-84-0 ]
  • [ 110-70-3 ]
Reference: [1] Journal of Polymer Science, 1959, vol. 40, p. 343,345
  • 15
  • [ 24424-99-5 ]
  • [ 110-70-3 ]
  • [ 112257-19-9 ]
YieldReaction ConditionsOperation in experiment
81% at 0 - 20℃; N, N'-Dimethylethylenediamine (5.00g, 57mmol) was dissolved in CH2Cl2 (25mL) and cooled to 0°C. Di-tert-butyl dicarbonate (5.00g, 22mmol) was dissolved in CH2Cl2 (25mL) and added dropwise to the reaction flask at 0°C, and then warmed to room temperature and stirred overnight. The reaction solution was quenched with H2O (20mL), and extracted with CH2Cl2 (40mL x 2), and the combined organic layers dried with Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel using CH3OH/CH2Cl2 (1/20, V/V) as eluent to give 2 as colorless oil (4.37g, 81percent), 1H NMR (400MHz, CDCl3) δ 3.39-3.36 (m, 2H, CH2), 2.95-2.90 (s, 3H, CH3), 2.76 (m, 2H, CH2), 2.48 (s, 3H, CH3), 1.48 (s, 9H, (CH3)3); HRMS (ESI) m/z [M+H]+ Calcd for C9H21N2O2+: 189.1603. Found: 189.1601.
74% at 20℃; for 16 h; To a stirred solution of Λ/,Λ/'-dimethylethylene diamine (3.66 mL, 34 mmol) in dichloromethane (40 mL) at 0°C was added dropwise a solution of di-tert-butyl dicarbonate (2.4 g, 11 mmol) in dichloromethane (20 mL) and allowed to warm to room temperature overnight, concentrated under reduced pressure, diluted with EtOAc (100 mL), washed with water (2 * 100 mL), brine (100 mL), dried and concentrated under reduced pressure to give the title product 91 as a colourless oil (1.54 g, 74percent yield). 1H NMR (400 MHz, CDCI3) δ 3.26 (t, J = 6.15 Hz, 2H), 2.81 (s, 3H), 2.66 (t, J = 6.57 Hz, 2H), 2.38 (s, 3H), 9.28 (s, 9H) ppm.
61% at 20℃; for 24 h; Example 71Synthesis of tert-butyl methyl [2-(methylamino)ethyl]carbamate (VI-I) A solution of di-tert-butyl dicarbonate (2.18 g, 0.01 mol) in CH2Cl2 (120 mL) was added dropwise to a solution of N,N'-Dimethyl-ethane-1,2-diamine (1.76 g, 0.02 mol) in CH2Cl2 (40 mL) over 6 h with vigorous stirring. The reaction mixture was continued to stir for a further 18 h at room temperature. Then the solvent was concentrated in vacuo to give an oily residue, which was dissolved in 60 mL of 2M Na2CO3 aqueous solution, and extracted with CH2Cl2 (30 mL x 2). The combined organic layers were washed with 2M Na2CO3 (30 mL x 2), and dried over anhydrous MgSO4. The solvent was evaporated in vacuo to yield the product, which was purified by column chromatography (silica gel, CH2Cl2 : MeOH, 9: 1) to afford colorless oil (VI-I, 1.15 g, 61percent)
61% at 20℃; for 24 h; Example 71Synthesis of tert-butyl methyl [2-(methylamino)ethyl]carbamate (VI-I) A solution of di-tert-butyl dicarbonate (2.18 g, 0.01 mol) in CH2Cl2 (120 mL) was added dropwise to a solution of N,N'-Dimethyl-ethane-1,2-diamine (1.76 g, 0.02 mol) in CH2Cl2 (40 mL) over 6 h with vigorous stirring. The reaction mixture was continued to stir for a further 18 h at room temperature. Then the solvent was concentrated in vacuo to give an oily residue, which was dissolved in 60 mL of 2M Na2CO3 aqueous solution, and extracted with CH2Cl2 (30 mL x 2). The combined organic layers were washed with 2M Na2CO3 (30 mL x 2), and dried over anhydrous MgSO4. The solvent was evaporated in vacuo to yield the product, which was purified by column chromatography (silica gel, CH2Cl2 : MeOH, 9: 1) to afford colorless oil (VI-I, 1.15 g, 61percent)
51% at 20℃; for 23 h; A solution of di-tert-butyl dicarbonate (4.95 g, 22.69 mmol) in CH2Cl2 (240 mL) was added dropwise to a stirred solution of N,N’-dimethylethane-1,2-diamine (4 g, 45.38 mmol) in CH2Cl2 (80 mL) over a period of 20h. The resulting mixture was stirred at r.t. for 3h. The mixture was then washed sequentially with sat. Na2CO3 (2 x 100 mL), water (50 mL), and sat. brine (50 mL). The organic solution was dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-10percent CH3OH in CH2Cl2 gave the title compound (2.177 g, 51percent) as a pale yellow oil; 1H NMR: 1.40 (9H, s), 2.28 (3H, s), 2.57 (2H, t), 2.79 (3H, s), 3.20 (2H, t).
24% With triethylamine In dichloromethane at 0 - 20℃; for 2.5 h; Preparation of N-tert-Butoxycarbonyl-N, N'-dimethylethylenediamine; Λ/,Λ/-dimethylethylenediamine (1.O g, 11.3 mmol) was dissolved in anhydrous dichloromethane (10 ml.) and was treated with triethylamine (1.6 ml_, 1 1.3 mmol). The mixture EPO <DP n="38"/>was cooled to 0 °C for the addition of di-terf-butyl dicarbonate (2.5 g, 1 1.3 mmol). The reaction stirred for 30 min at 0 °C then 2 hours at room temperature. The reaction mixture was then washed with water (10 ml.) and the aqueous layer extracted with further portions of dichloromethane (2 x 10 ml_). The combined organic phases were dried over NaaSCu and the solvent removed in vacuo. Purification by column chromatography (40:8:1 , dichloromethane:methanol:aqueous ammonia) yielded (508 mg, 24 percent) of the desired N-tert- butoxycarbonyl-N,N'-dimethylethylenediamine as a colourless oil.
17%
Stage #1: at 0 - 20℃;
Stage #2: With ammonium chloride In ethyl acetate
Preparation of Methyl-(2-methylamino-ethyl)-carbamic acid tert-butyl esterTo an ice-cooled solution of N,N'-dimethyethylenediamine (10 ml_, 91.0 mmol) in dry THF (150 ml.) was added a solution of BoC2O (4.97 g, 22.8 mmol) in dry THF (50 ml.) over 30 minutes. The reaction mixture was stirred for 1 h at 00C then at rt overnight, and concentrated in vacuo. The resulting residue was taken up in a mixture of EA and a sat.NH4CI solution. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. FC (10 percent MeOH in DCM) afforded the title compound as a yellow oil (2.90 g, 17percent). LC-MS (analytic A, Zorbax SB-AQ column, acidic conditions): tR = 0.50 min; [M+H]+ 189.40.
17% at 0 - 20℃; To an ice-cooled solution of N,N'-dimethyethylenediamine (10 mL, 91.0 mmol) in dry THF (150 mL) was added a solution of Boc2O (4.97 g, 22.8 mmol) in dry THF (50 mL) over 30 minutes. The reaction mixture was stirred for 1 h at 0° C. then at rt overnight, and concentrated in vacuo. The resulting residue was taken up in a mixture of EA and a sat. NH4Cl solution. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. FC (10percent MeOH in DCM) afforded the title compound as a yellow oil (2.90 g, 17percent).LC-MS (analytic A, Zorbax SB-AQ column, acidic conditions): tR=0.50 min; [M+H]+=189.40.
6.8 g at 0 - 20℃; for 18 h; To a solution of N,N'-dimethylethane-l,2-diamine (40.4 g) in DCM (300 mL) was added a solution of Boc20 (10 g, 10.6 mL, 45.8 mmol) in DCM (100 mL) dropwise at 0 °C over 1 hr. The reaction mixture was stirred at room temperature for 18 hrs. The organic layer was washed with saturated aqueous NaHC03 (50 mL), brine (50 mL), dried over Na2S04 and concentrated in vacuo. The residue was purified by column chromatography to afford ie/t-butyl N-methyl-N-[2- (methylamino)ethyl]carbamate (6.8 g, Compound BC-1) as a yellow oil. 1H NMR (400MHz, CDC13) δ ppm: 3.34 (br. s., 2H), 2.89 (s, 3H), 2.74 (t, / = 6.7 Hz, 2H), 2.46 (s, 3H), 1.47 (s, 9H).
2.1 g at 0 - 25℃; for 4 h; Add in a 100mL single-mouth bottleN1,N2-dimethylethyl-1,2-diamine (4g, 45mmol), cooled to about 0 °C in an ice bath,Then (Boc) 2O (5 g, 23 mmol) in DCM (20 mL)The temperature was raised to 25 ° C and the reaction was stirred for 4 h.Concentrated under reduced pressure, a saturated sodium carbonate solution was added to the residue, and extracted three times with ethyl acetate (30 mL×3).The organic phase was combined, washed three times with saturated brine (20 mL×3) and dried over anhydrous sodiumThe mixture was suction filtered under reduced pressure, and the filtrate was evaporated.The crude product was purified by column chromatography eluting with EtOAc EtOAcConcentration under reduced pressure gave 2.1 g of a yellow oil.

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  • 17
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