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Chemical Structure| 10111-08-7
Chemical Structure| 10111-08-7
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Product Details of [ 10111-08-7 ]

CAS No. :10111-08-7 MDL No. :MFCD00003544
Formula : C4H4N2O Boiling Point : -
Linear Structure Formula :- InChI Key :XYHKNCXZYYTLRG-UHFFFAOYSA-N
M.W :96.09 Pubchem ID :24955
Synonyms :

Calculated chemistry of [ 10111-08-7 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 23.98
TPSA : 45.75 Ų

Pharmacokinetics

GI absorption : High
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) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.09
Log Po/w (XLOGP3) : -0.14
Log Po/w (WLOGP) : 0.22
Log Po/w (MLOGP) : -1.44
Log Po/w (SILICOS-IT) : 1.2
Consensus Log Po/w : -0.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.81
Solubility : 14.9 mg/ml ; 0.155 mol/l
Class : Very soluble
Log S (Ali) : -0.37
Solubility : 41.3 mg/ml ; 0.43 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.1
Solubility : 7.69 mg/ml ; 0.08 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 10111-08-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10111-08-7 ]

* 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 [ 10111-08-7 ]
  • Downstream synthetic route of [ 10111-08-7 ]

[ 10111-08-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 10111-08-7 ]
  • [ 3724-26-3 ]
YieldReaction ConditionsOperation in experiment
78% at 5 - 20℃; for 3 h; To a solution of compound 1 H-imidazole-2-carbaldehyde (5g, 52.08 mmol) in MeOH (50 mL) was added sodium borohydride (3.93g, 104.16 mmol) portion-wise, at 5 00, and the reaction mixture was allowed to stir at RT for 3h. The reaction mixture was quenched with brine (25 mL) and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 10percent MeOH/CHCI3) to obtain (1H-imidazol-2-yl)-methanol as a pale yellow solid (4g, 78percent).R:0.1 (10percent MeOH/CHCI3).1H NMR (400MHz, CD3OD): O 6.97 (5, 2H), 4.61 (5, 2H).
51% With sodium tetrahydroborate In methanol at 20℃; for 1 h; Inert atmosphere To a solution of 2-imidazolecarboxyaldehyde (18-1) (1.92 g, 20 mmol, 1.0 eq.) was suspended in methanol (30 ml), NaBH4 (1.52g, 40 mmol, 2.0 eq.) was added portion-wise. The reaction mixture was stirred at room temperature for 1 h under N2. It was quenched with 5 ml of brine. The solvent was removed and the solid was purified with silica gel column chromatography (DCM : MeOH = 20: 1) to afford 18-2 as a white solid. (1.0g, Yield: 51percent).
51% at 20℃; for 1 h; Inert atmosphere Compound 26-2 (0449) To a solution of 2-imidazolecarboxyaldehyde (26-1) (1.92 g, 20 mmol, 1.0 eq) was suspended in methanol (30 mL), NaBH4 (1.52 g, 40 mmol, 2.0 eq) was added portion-wise. The reaction mixture was stirred at room temperature for 1 h under N2. It was quenched with 5 mL of brine. The solvent was removed and the solid was purified with silica gel column chromatography (DCM:MeOH=20:1) to afford a white solid. (1.0 g, Yield: 51percent).
45.2% With sodium tetrahydroborate In methanol; dichloromethane Part A
Preparation 2-hydroxymethyl-1H-imidazole
2-Imidazolecarboxyaldehyde (5.0 g, 52.0 mmol) was suspended in 200 mL of methanol. NaBH4 (3.95 g, 0.10 mol) was added portion-wise.
The reaction mixture was stirred at room temperature for 1 h under N2.
It was quenched with 10 mL of brine.
The solvent was removed.
The solid was washed with 5percent MeOH in CH2Cl2.
The inorganic solid was filtered off.
The filtrate was concentrated and chromatographed with 5percent MeOH in CH2Cl2 to give 2.32 g off-white solid (45.2percent yield).
1H NMR (DMSO-d6): δ 6.86 (s, 2H), 4.40 (s, 2H).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 827 - 833
[2] Patent: WO2015/36759, 2015, A1, . Location in patent: Page/Page column 200
[3] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3208 - 3213
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5849 - 5853
[5] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 302
[6] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1729 - 1744
[7] Patent: US2003/144287, 2003, A1,
[8] Biological and Pharmaceutical Bulletin, 1998, vol. 21, # 9, p. 958 - 963
[9] Journal of Medicinal Chemistry, 2004, vol. 47, # 15, p. 3707 - 3709
  • 2
  • [ 10111-08-7 ]
  • [ 16042-25-4 ]
YieldReaction ConditionsOperation in experiment
97.5% With dihydrogen peroxide In water at 20℃; for 72 h; An aqueous 30percent H2O2 solution (10g) was added dropwise to a stirred solution of imidazole-2-carboxaldehyde (2.88g 0.030mol) in water (10ml). The reaction was allowed to proceed at room temperature for 72h, following which the water was removed in vacuo at room temperature to afford a white crystalline solid. This solid was washed with a stirred mixture of diethylether/water (4:1) to remove the excess peroxide. Note: heating causes decarboxylation. Yield: 97.5percent. Mp=156–158°C. δH (400MHz, D2O): 7.56 (2H, s, Im-H); δC (400MHz, D2O): 158.86, 141.02, 120.49ppm. IR ν (KBr): 3392(m), 3124(m), 2861(m), 1618(s), 1502(m), 1462(m), 1421(s), 1388(s), 1322(m), 1108(s), 925(s), 910(s), 819(m), 797(s), 774(m) cm−1. Anal. Calc. for C4H6N2O3 (130.11); C, 36.92; H, 4.65; N, 21.53percent. Found: C, 37.18; H, 4.94; N, 21.47percent.
Reference: [1] Journal of Inorganic Biochemistry, 2015, vol. 145, p. 11 - 18
  • 3
  • [ 16681-56-4 ]
  • [ 68-12-2 ]
  • [ 10111-08-7 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5 h;
Stage #3: at -20℃; for 0.5 h;
To a solution of 2-bromo-1H-imidazole (0.65 g, 4.4 mmol, 1.0 equiv.)in dry THF (20 mL) at 0 C was added a 2 M solution of i-PrMgCl in THF (2.2 mL, 4.4 mmol,1.0 equiv.) during 5 min. The clear solution was stirred at that temperature for an additional5 min, and a 2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) was addeddropwise during 5 min, while maintaining the temperature below 20 C. The resulting mixturewas stirred at that temperature for 0.5 h, dry DMF (0.32 g, 4.4 mmol, 1.0 equiv.) was added to20 C. The resulting mixture was warmed to 20 C in 0.5 h and quenched with water (6 mL).After stirring the mixture below 20 C for 10 min, the phases were separated and the water phasewas extracted one additional time with ethyl acetate. The resulting suspension was allowed to reachroom temperature and fitered through a 0.5 1cm pad of silica gel eluted with 10 mL of ethyl acetate.The filtrate was concentrated and the residue was purified by flash chromatography on silica gel(eluent: petroleum ether/ethyl acetate = 10:1) to afford product 3k as pale yellow solid, 0.38 g (yield:91percent), m.p.: 205–206 C. 1H-NMR (600 MHz, DMSO) 13.60 (s, 1H), 9.64 (s, 1H), 7.42 (s, 2H). 13C-NMR(151 MHz, DMSO) 181.66, 146.09.1H-Imidazole-4-carbaldehyde (3l): To a
Reference: [1] Molecules, 2017, vol. 22, # 11,
  • 4
  • [ 78667-05-7 ]
  • [ 10111-08-7 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 23, p. 6264 - 6267
  • 5
  • [ 67478-50-6 ]
  • [ 10111-08-7 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1990, vol. 109, # 6, p. 388 - 395
[2] European Journal of Organic Chemistry, 2011, # 30, p. 6092 - 6099
[3] Tetrahedron, 1999, vol. 55, # 26, p. 8111 - 8128
  • 6
  • [ 65276-01-9 ]
  • [ 10111-08-7 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3208 - 3213
  • 7
  • [ 1582276-25-2 ]
  • [ 132-32-1 ]
  • [ 10111-08-7 ]
Reference: [1] Dalton Transactions, 2014, vol. 43, # 14, p. 5269 - 5273
  • 8
  • [ 107-31-3 ]
  • [ 10111-08-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 2, p. 611 - 620
  • 9
  • [ 10111-08-7 ]
  • [ 31722-49-3 ]
YieldReaction ConditionsOperation in experiment
89% With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid In acetonitrile for 14 h; Reflux General procedure: 4-Isopropylbenzaldehyde 1a (0.50 g, 3.37 mmol), acetohydroxamic acid (0.30 g, 4.05 mmol), acetonitrile (5 ml), and Bi(OTf)3 (0.11 g, 0.17 mmol) were taken into a 25 ml round-bottomed flask fitted with a condenser and calcium chloride guard tube. The mixture was refluxed for 14 h and after completion of the reaction (GC, 10percent SE-30 on Chromosorb, 10' .x. 1/8 column), the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product obtained was purified by normal column chromatography(silica gel 100-200 mesh, ethyl acetate/hexane = 1:20) to obtain 4-isopropylbenzonitrile 3a (0.47 g, 97percent).
41% With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In N,N-dimethyl-formamide at 100℃; for 4 h; Compound 234.1. lH-Imidazole-2-carbonitrile. Into a 1-L round-bottom flask, was placed a solution of lH-imidazole-2-carbaldehyde (5 g, 52.04 mmol) in NN- dimethylformamide (200 mL). Triethylamine (10.8 mL, 77.97 mmol), hydroxylamine hydrochloride (3.95 g, 56.84 mmol, 1.10 equiv), 1-propanephosphonic anhydride solution and 2,4,6-tripropyl-l,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution (T3P) (36.4 g, 114.40 mmol) were added to the reaction. The reaction mixture was stirred for 4h at 100 °C, cooled and then quenched with 500 mL of water/ice. The aqueous phase was extracted with 3 x 1L of ethyl acetate, then the combined organic layers was washed with 2 x 1L of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/2) as eluent to furnish 2 g (41percent) of the title compound as an off-white solid.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 27, p. 3421 - 3424
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3038 - 3041
[3] Patent: WO2015/95767, 2015, A1, . Location in patent: Page/Page column 271; 272
[4] Patent: WO2012/85038, 2012, A1, . Location in patent: Page/Page column 39
  • 10
  • [ 10111-08-7 ]
  • [ 74-88-4 ]
  • [ 13750-81-7 ]
YieldReaction ConditionsOperation in experiment
59% With potassium carbonate In ethanol; N,N-dimethyl-formamide at 50℃; for 5 h; Stir at room temperature To a solution of 1H-imidazole-2-carbaldehyde (250 mg, 2.6 mmol) and K2CO3 (431 mg, 3.12 mmol) in DMF (2.5 mL) was added methyl iodide (442 mg, 3.12 mmol). The mixture was stirred at 50° C. for 5 h and allowed to cool to remove solids. Water was added to the filtrate and extracted three times with ethyl acetate. The combined extracts were washed with saturated saline and dried over anhydrous sodium sulfate. The mixture was concentrated by suction and filtered to give 1-methyl-1H-imidazole-2-carboxaldehyde as a pale yellow oil (168 mg, yield 59percent).
Reference: [1] Patent: CN103570683, 2018, B, . Location in patent: Paragraph 0711; 0715-0717
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386
[3] Chemico-Biological Interactions, 2016, vol. 259, p. 85 - 92
  • 11
  • [ 74-83-9 ]
  • [ 10111-08-7 ]
  • [ 13750-81-7 ]
Reference: [1] Bioconjugate Chemistry, 2010, vol. 21, # 6, p. 1032 - 1042
[2] Inorganica Chimica Acta, 2012, vol. 389, p. 168 - 175
  • 12
  • [ 75-03-6 ]
  • [ 10111-08-7 ]
  • [ 111851-98-0 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5 h; To a suspension of 1H-imidazole-2-carbaldehyde (480 mg, 5 mmol) and potassium carbonate (936 mg, 6 mmol) in N,N-dimethylformamide (7 mL) was added iodoethane (829 mg, 6 mmol) and the mixture was heated at 50° C. for 5 hrs. Solvent was removed under reduced pressure. The residue was partitioned between water (30 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (20 mL.x.3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 1-ethyl-1H-imidazole-2-carbaldehyde as light yellow oil (520 mg, yield 84percent). 1H NMR (400 MHz, CDCl3) δ (ppm): 1.42-1.46 (t, J=7.2 Hz, 3H), 4.42-4.47 (q, 2H), 7.19 (s, 1H), 7.29 (s, 1H), 9.82 (s, 1H). LC-MS (ESI) m/z: 125 (M+1)+.
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386
[2] Patent: US2010/35883, 2010, A1, . Location in patent: Page/Page column 70-71
[3] Patent: EP1422228, 2004, A1, . Location in patent: Page 223
[4] Patent: EP1550657, 2005, A1, . Location in patent: Page/Page column 84
[5] Chemico-Biological Interactions, 2016, vol. 259, p. 85 - 92
[6] Patent: WO2009/67233, 2009, A1, . Location in patent: Page/Page column 34
  • 13
  • [ 74-96-4 ]
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  • [ 111851-98-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4713 - 4726
[2] Journal of Biological Chemistry, 2011, vol. 286, # 22, p. 19422 - 19430
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