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[ CAS No. 149520-94-5 ] {[proInfo.proName]}

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Chemical Structure| 149520-94-5
Chemical Structure| 149520-94-5
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Product Details of [ 149520-94-5 ]

CAS No. :149520-94-5 MDL No. :MFCD09864446
Formula : C6H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NGJGNTZJCFFZLK-UHFFFAOYSA-N
M.W :155.15 Pubchem ID :573233
Synonyms :

Calculated chemistry of [ 149520-94-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 39.08
TPSA : 81.0 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) : -7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.89
Log Po/w (XLOGP3) : 0.27
Log Po/w (WLOGP) : 0.18
Log Po/w (MLOGP) : -0.58
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.11
Solubility : 12.0 mg/ml ; 0.0775 mol/l
Class : Very soluble
Log S (Ali) : -1.53
Solubility : 4.55 mg/ml ; 0.0294 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.34
Solubility : 7.04 mg/ml ; 0.0454 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 149520-94-5 ]

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 [ 149520-94-5 ]

* 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 [ 149520-94-5 ]
  • Downstream synthetic route of [ 149520-94-5 ]

[ 149520-94-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 109-12-6 ]
  • [ 70-23-5 ]
  • [ 149520-94-5 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: at 75℃;
Stage #2: With hydrazine hydrate In ethanol at 75℃;
To a mixture of imidazo[l,2-a]pyrimidine-2-carboxylic acid ethyl ester and imidazo[l,2-a]pyrimidine-3-carboxylic acid ethyl ester (500 mg, 2.62 mmol, 1.0 eq) in EtOH ( 20 mL) was added hydrazine hydrate (180 mg, 2.88 mmol, 1.1 eq). The reaction mixture was heated at 75 °C overnight. The reaction mixture was concentrated and the resulting residue was purified by chromatography on a silica gel column (DCM/MeOH = 20/1, v/v) to give 2-amino-lH-imidazole-4-carboxylic acid ethyl ester (220 mg, 54percent) as a yellow solid.
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5620 - 5628
[2] Patent: WO2018/11628, 2018, A1, . Location in patent: Paragraph 00267
  • 2
  • [ 64951-07-1 ]
  • [ 149520-94-5 ]
YieldReaction ConditionsOperation in experiment
100% With hydrazine In ethanol at 75℃; for 16 h; To a stirred solution of ethyl imidazo[l ,2-α]pyrimidine-2-carboxylate or ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (1 g, 5.2 mmol) in ethanol (40 mL) was added hydrazine monohydrate (0.28 mL, 5.7 mmol). The reaction was heated to 75 °C for 16 h and was concentrated under reduced pressure. The resulting light yellow solid was suspended in diethyl ether and filtered to collect ethyl 2-amino-1H-imidazole-4- carboxylate (800 mg, 100percent) as a white solid. [00243] 1E NMR (400 MHz, CD3OD) 5 7.27 (s, 1H), 4.24 (q, J= 7.0 Hz, 2H), 1.31(t, J= 7.0 Hz, 3H).[00244] 13C NMR (500 MHz, CD3OD) δ 165.5, 156.1, 131.8, 125.7, 63.8, 17.3.[00245] HPLC Phenomenex LUNA C- 18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 0.46 min, 100percent homogeneity index.[00246] Anal. Calcd for C6H9N3O2: C, 46.44; H, 5.84; N5 27.08. Found: C, 46.17;H, 5.65; N, 27.28.[00247] HRMS: Anal. Calcd. for C6Hi0N3O2 156.0773 found: 156.0779 (M+H)+.
Reference: [1] Patent: WO2006/71752, 2006, A1, . Location in patent: Page/Page column 84
  • 3
  • [ 64951-06-0 ]
  • [ 149520-94-5 ]
YieldReaction ConditionsOperation in experiment
100% With hydrazine In ethanol at 75℃; for 16 h; To a stirred solution of ethyl imidazo[l ,2-α]pyrimidine-2-carboxylate or ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (1 g, 5.2 mmol) in ethanol (40 mL) was added hydrazine monohydrate (0.28 mL, 5.7 mmol). The reaction was heated to 75 °C for 16 h and was concentrated under reduced pressure. The resulting light yellow solid was suspended in diethyl ether and filtered to collect ethyl 2-amino-1H-imidazole-4- carboxylate (800 mg, 100percent) as a white solid. [00243] 1E NMR (400 MHz, CD3OD) 5 7.27 (s, 1H), 4.24 (q, J= 7.0 Hz, 2H), 1.31(t, J= 7.0 Hz, 3H).[00244] 13C NMR (500 MHz, CD3OD) δ 165.5, 156.1, 131.8, 125.7, 63.8, 17.3.[00245] HPLC Phenomenex LUNA C- 18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 0.46 min, 100percent homogeneity index.[00246] Anal. Calcd for C6H9N3O2: C, 46.44; H, 5.84; N5 27.08. Found: C, 46.17;H, 5.65; N, 27.28.[00247] HRMS: Anal. Calcd. for C6Hi0N3O2 156.0773 found: 156.0779 (M+H)+.
Reference: [1] Patent: WO2006/71752, 2006, A1, . Location in patent: Page/Page column 84
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