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[ CAS No. 652-37-9 ] {[proInfo.proName]}

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Chemical Structure| 652-37-9
Chemical Structure| 652-37-9
Structure of 652-37-9 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 652-37-9 ]

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Product Details of [ 652-37-9 ]

CAS No. :652-37-9 MDL No. :MFCD00022832
Formula : C9H10N4O4 Boiling Point : -
Linear Structure Formula :- InChI Key :HCYFGRCYSCXKNQ-UHFFFAOYSA-N
M.W :238.20 Pubchem ID :69550
Synonyms :
Acefylline

Calculated chemistry of [ 652-37-9 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.62
TPSA : 99.12 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) : -8.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.03
Log Po/w (XLOGP3) : -0.76
Log Po/w (WLOGP) : -1.48
Log Po/w (MLOGP) : -0.72
Log Po/w (SILICOS-IT) : -1.21
Consensus Log Po/w : -0.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.1
Solubility : 19.0 mg/ml ; 0.0798 mol/l
Class : Very soluble
Log S (Ali) : -0.84
Solubility : 34.1 mg/ml ; 0.143 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.07
Solubility : 205.0 mg/ml ; 0.861 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 652-37-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 652-37-9 ]

* 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 [ 652-37-9 ]
  • Downstream synthetic route of [ 652-37-9 ]

[ 652-37-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 7029-96-1 ]
  • [ 652-37-9 ]
YieldReaction ConditionsOperation in experiment
91% With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 2 h; General procedure: LiOH·H2O (1.5 equiv) was added portion wise to a stirred solution of ester compounds 2a–2b (1.0 equiv) in THF (10vol) and H2O (10vol) at room temperature and the reaction mixture was stirred for 2h. As monitored by TLC, from the reaction mixture THF was concentrated and acidified with aqueous KHSO4 solution, extracted with 5percent methanol and dichloromethane. The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to afford the desired solid products 3a–3b. 4.2.3
2-(1,3-Dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl) acetic acid (3a)
Compound 2a (5 g, 18.78 mmol), LiOH·H2O (1.18 g, 28.18 mmol) in 100 mL of THF:H2O (1:1) to afford 3a (4.1 g, 91percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 13.27 (brs, 1H), 8.04 (s, 1H), 5.07 (s, 2H), 3.44 (s, 3H), 3.20 (s, 3H); m/z (ES)+: 239.04 [M+H]+
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 379 - 396
[2] MedChemComm, 2017, vol. 8, # 1, p. 176 - 183
[3] Ricerca Scientifica, 1952, vol. 22, p. 1596,1599
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 14, p. 2527 - 2534
[5] Heterocyclic Communications, 2015, vol. 21, # 1, p. 13 - 18
  • 2
  • [ 7597-60-6 ]
  • [ 3926-62-3 ]
  • [ 652-37-9 ]
YieldReaction ConditionsOperation in experiment
91.5%
Stage #1: With sodium hydroxide In water at 90 - 95℃; for 0.5 h;
Stage #2: With sodium carbonate In water at 55 - 65℃; for 2.5 h;
Into a 3L reaction bottle, 1500 ml of pure water and 44 g (l. Heating up to 40 ° C, the input of 198g (1. Omol) N, N-1,3-dimethyl-4-amino-5-formyl urea urea (referred to as dimethyl FAU, Shanghai Pharmaceutical Co., ). Continue to heat up to 90 ° C, measured liquid PH value of 11, at 90 ~ 95 ° C for half an hour, sodium chloroacetate 128g (1. lmol) dissolved in 500g of pure water solution, down to 55 ~ 65 ° C, Dropping an aqueous solution of sodium chloroacetate for about 0.5 h, clarifying the solution and adding 20percent aqueous solution of Na2CO3 to keep the pH of the reaction liquid at 8 to 12 and keeping it at 55 to 65 ° C while adding TLC254 to detect theophylline sodium salt Until the raw material point theophylline sodium salt completely disappeared (Rf = 0.7; Rfigss ^ = 0.4), reaction 2 hours, repeat the measurement of PH: 8 ~ 12.Cooling to 60 ~ 65 ° C by adding 50percent sulfuric acid, adjust the PH of 2 ~ 2. 5, a large number of white solid precipitation, stirring for half an hour re-measured PH value unchanged. And then filter the mother liquor, the wet goods into 1000ml of pure water, heated to 50 ~ 55 ° C hot filter, and then the amount of 50 ~ 55 ° C pure water washing, drying, in acetic acid theophylline finished 218g, yield 91. 5percent, HPLC content of 99. 95percent.
Reference: [1] Patent: CN103360393, 2016, B, . Location in patent: Paragraph 0036-0040
  • 3
  • [ 58-55-9 ]
  • [ 79-11-8 ]
  • [ 652-37-9 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 1, p. 37 - 40
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 1320
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 1321
  • 4
  • [ 58-55-9 ]
  • [ 652-37-9 ]
Reference: [1] Heterocyclic Communications, 2015, vol. 21, # 1, p. 13 - 18
[2] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 379 - 396
[3] MedChemComm, 2017, vol. 8, # 1, p. 176 - 183
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