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[ CAS No. 37527-48-3 ] {[proInfo.proName]}

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Chemical Structure| 37527-48-3
Chemical Structure| 37527-48-3
Structure of 37527-48-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 37527-48-3 ]

CAS No. :37527-48-3 MDL No. :MFCD12755941
Formula : C5H3ClN4O Boiling Point : -
Linear Structure Formula :- InChI Key :DCOLIWSXJIHGOF-UHFFFAOYSA-N
M.W : 170.56 Pubchem ID :57659203
Synonyms :

Calculated chemistry of [ 37527-48-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 39.52
TPSA : 74.43 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.93
Log Po/w (XLOGP3) : 0.14
Log Po/w (WLOGP) : 0.3
Log Po/w (MLOGP) : -0.12
Log Po/w (SILICOS-IT) : 1.95
Consensus Log Po/w : 0.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.59
Solubility : 4.37 mg/ml ; 0.0256 mol/l
Class : Very soluble
Log S (Ali) : -1.26
Solubility : 9.38 mg/ml ; 0.055 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.353 mg/ml ; 0.00207 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.67

Safety of [ 37527-48-3 ]

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 [ 37527-48-3 ]

* 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 [ 37527-48-3 ]
  • Downstream synthetic route of [ 37527-48-3 ]

[ 37527-48-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 4316-98-7 ]
  • [ 530-62-1 ]
  • [ 37527-48-3 ]
YieldReaction ConditionsOperation in experiment
96% for 0.833333 h; Reflux; Inert atmosphere Preparation 131
6-Chloro-7,9-dihydro-purin-8-one
Combine 6-chloro-pyrimidine-4,5-diamine (7.46 mmol; 1.08 g); 1,1'-carbonyldiimidazole (2 equiv; 14.92 mmol; 2.42 g) and 1,4-dioxane (20 mL) and heat to reflux under nitrogen for 50 min.
Evaporate the yellow solution to an oil.
Add DCM (80 mL), let sit 1 h, filter and dry in vacuum oven at 45° C. to provide the title compound (1.22 g; 7.15 mmol; 96percent) MS (ES+): m/z=169 (M-H).
86% for 48 h; Heating / reflux 2D. 6-Chloro-7,9-dihydropurin-8-one; A mixture of the 5,6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N,N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under <n="119"/>argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86percent) LC/MS (LCTl): Rt 2.45 [M+H]+ 173, 171.
86% for 48 h; Heating / reflux 13B. 6-Chloro-7,9-dihydropurin-8-one <n="118"/>A mixture of the 5,6-diamino-4-chloropyrimidine of Example 13A (1.0 g, 6.92 mmol) and N,N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86percent) LC/MS (LCT1): Rt 2.45 [M+H]+ 173, 171.
86% for 48 h; Heating / reflux 6B. 6-Chloro-7,9-dihydropurin-8-oneA mixture of the 5,6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N,N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86percent) LC/MS (LCTl): Rt2.45 [M+H]+ 173, 171.

Reference: [1] Patent: US2010/120801, 2010, A1, . Location in patent: Page/Page column 22
[2] Patent: WO2008/75110, 2008, A1, . Location in patent: Page/Page column 116-117
[3] Patent: WO2007/125315, 2007, A2, . Location in patent: Page/Page column 115-116
[4] Patent: WO2007/125325, 2007, A1, . Location in patent: Page/Page column 93
[5] Patent: WO2006/46023, 2006, A1, . Location in patent: Page/Page column 116
  • 2
  • [ 4316-98-7 ]
  • [ 74124-79-1 ]
  • [ 37527-48-3 ]
YieldReaction ConditionsOperation in experiment
78% for 16 h; Heating / reflux Synthesis 20-1 -A; 6-Chloro-7H-purin-8(9H)-one; NXrNH2 A mixture of 4-chloropyrimidine-2,3-diamine (36 mg, 0.25 mmol) and di(/V-succinimidyl)carbonate (128 mg, 0.50 mmol) in acetonitrile (10 mL) was refluxed for 16 hours. The solids formed were collected, washed with acetonitrile (2 x 5 mL) and dried, to give the title compound as a light yellow powder (33 mg, 78percent).1H NMR (500 MHz, de-DMSO) δ 8.35 (1 H, s), 11.90 (2H, s, broad); LC-MS (2) R1 1.96 min; m/z (ESI) 171 [MH+].
Reference: [1] Patent: WO2008/75007, 2008, A1, . Location in patent: Page/Page column 113
  • 3
  • [ 19916-15-5 ]
  • [ 37527-48-3 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 6671,6675
  • 4
  • [ 13231-00-0 ]
  • [ 37527-48-3 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 6671,6675
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