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[ CAS No. 634-97-9 ] {[proInfo.proName]}

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Chemical Structure| 634-97-9
Chemical Structure| 634-97-9
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Product Details of [ 634-97-9 ]

CAS No. :634-97-9 MDL No. :MFCD00005219
Formula : C5H5NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WRHZVMBBRYBTKZ-UHFFFAOYSA-N
M.W : 111.10 Pubchem ID :12473
Synonyms :

Calculated chemistry of [ 634-97-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 27.75
TPSA : 53.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.7
Log Po/w (XLOGP3) : 0.85
Log Po/w (WLOGP) : 0.71
Log Po/w (MLOGP) : -0.36
Log Po/w (SILICOS-IT) : 0.82
Consensus Log Po/w : 0.54

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.46
Solubility : 3.85 mg/ml ; 0.0346 mol/l
Class : Very soluble
Log S (Ali) : -1.55
Solubility : 3.14 mg/ml ; 0.0283 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.92
Solubility : 13.4 mg/ml ; 0.12 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 634-97-9 ]

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 [ 634-97-9 ]

* 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 [ 634-97-9 ]
  • Downstream synthetic route of [ 634-97-9 ]

[ 634-97-9 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 109-97-7 ]
  • [ 124-38-9 ]
  • [ 931-03-3 ]
  • [ 634-97-9 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4512 - 4514
  • 2
  • [ 67-56-1 ]
  • [ 634-97-9 ]
  • [ 1193-62-0 ]
YieldReaction ConditionsOperation in experiment
85% at 0 - 35℃; for 24.5 h; To a solution of pyrrole-2-carboxylic acid (1) (16.65 g, 0.15 mol)in 10 mL of MeOH was added 50 mL of SOCl2 dropwise within30 min at 0 C. Subsequently, the reaction mixture was stirred at35 C for 24 h. Then, the solvent was evaporated in vacuo, andthe residue was purified by column chromatography using ethylacetate/petroleum ether as eluent, giving intermediate 2 as a whitesolid, yield 85percent, mp: 72–73 C.
79% With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20 - 60℃; for 72 h; Example 36-1
Preparation for methyl 1H-pyrrole-2-carboxlate
A suspension of 1H-pyrrole-2-carboxylic acid (5.5g, 49.5mmol), WSCI*HCl (12.2g, 63.6mmol), HOBt (8.4g, 62.2mmol), methanol (7.0g, 218mmol) and 4-dimethylaminopyridine (3.0g, 24.5mmol) in dimethylformamide (60ml) was stirred for 70 hours at room temperature and for 2 hours at 60°C.
To the reaction mixture was added an aqueous 5percent potassium hydrogensulfate solution and the mixture was extracted with ethyl acetate/toluene (1/1)..
The organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution, and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate..
The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=5:13:1) to give the subject compound (4.88g, 79percent).1H NMR (CDCl3, 400 MHz) δ 9. 08 (brs, 1 H), 6. 90 - 6. 98 (m, 2 H), 6.25 - 6.29 (m, 1 H), 3.86 (s, 3 H).
65% With chloro-trimethyl-silane In methanol at 20℃; Method I Synthesis of 5-tert-Butyl-3-(3-p-tolyl-ureido)-1H-pyrrole-2-carboxylic acid methyl ester. (Example 24) [Show Image] Step 1; Chlorotrimethylsilane (17.9 mL, 141 mmol, 2.5 equiv) is added in one portion to a solution of pyrrole-2-carboxylic acid (6.28 g, 56.5 mmol) in dry methanol (100 mL) under N2 at rt. After stirring overnight, the reaction mixture is concentrated in vacuo, redissolved in dichloromethane, washed with water, dried (Na2SO4) and concentrated to give 4.62 g of methyl pyrrole-2-carboxylate as a tannish semi-crystalline solid (65percent), which was used without further purification. 1H NMR (CDCl3) d 9.3 (br s, 1H), 6.96 (br m, 1H), 6.92 (br m, 1H), 6.29 (br q, 1H), 3.86 (s, 3H).
65% at 20℃; To a solution of pyrrole-2-carboxylic acid (6.28 g, 56.5 mmol) in anh. MeOH (100 mL) under N2 at room temp. was added TMSCl (17.9 mL, 141 mmol, 2.5 equiv) in one portion. After stirring overnight, the reaction mixture was concentrated under reduced pressure, redissolved in CH2Cl2, washed with water, dried (Na2SO4) and concentrated to give methyl pyrrole-2-carboxylate as a tannish semi-crystalline solid (4.62 g, 65percent): 1H NMR (CDCl3) δ 3.86 (s, 3H), 6.29 (br q, 1H), 6.92 (br m, 1H), 6.96 (br m, 1H), 9.30 (br s, 1H). This material was used in the next step without further purification.

Reference: [1] Canadian Journal of Chemistry, 2002, vol. 80, # 12, p. 1662 - 1667
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 7091 - 7100
[3] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 20, p. 2997 - 3003
[4] Patent: EP1386913, 2004, A1, . Location in patent: Page 88
[5] Patent: EP986382, 2008, B1, . Location in patent: Page/Page column 23
[6] Patent: EP1019040, 2004, B1, . Location in patent: Page/Page column 31
[7] Journal of Natural Products, 2012, vol. 75, # 10, p. 1765 - 1776
[8] Patent: WO2006/23844, 2006, A2, . Location in patent: Page/Page column 92
  • 3
  • [ 634-97-9 ]
  • [ 1193-62-0 ]
Reference: [1] Chemische Berichte, 1911, vol. 44, p. 3168
[2] Patent: US6344476, 2002, B1,
[3] Patent: US4282242, 1981, A,
[4] Patent: US6187799, 2001, B1,
[5] Patent: US6335445, 2002, B1, . Location in patent: Page column 106
  • 4
  • [ 61985-23-7 ]
  • [ 634-97-9 ]
  • [ 1193-62-0 ]
  • [ 484-73-1 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 46, p. 8851 - 8859
  • 5
  • [ 186581-53-3 ]
  • [ 634-97-9 ]
  • [ 1193-62-0 ]
Reference: [1] Tetrahedron, 1992, vol. 48, # 8, p. 1457 - 1464
[2] Justus Liebigs Annalen der Chemie, 1955, vol. 593, p. 91,109
[3] Journal of the Chemical Society, 1958, p. 4458,4462
[4] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1475 - 1480
[5] Chemistry Letters, 1991, # 9, p. 1541 - 1542
[6] Tetrahedron Letters, 2002, vol. 43, # 14, p. 2589 - 2592
  • 6
  • [ 186581-53-3 ]
  • [ 684-93-5 ]
  • [ 634-97-9 ]
  • [ 1193-62-0 ]
Reference: [1] Patent: US2001/47006, 2001, A1,
[2] Patent: US2002/6943, 2002, A1,
  • 7
  • [ 7087-68-5 ]
  • [ 634-97-9 ]
  • [ 74-88-4 ]
  • [ 1193-62-0 ]
Reference: [1] Patent: US4675186, 1987, A,
  • 8
  • [ 634-97-9 ]
  • [ 74-88-4 ]
  • [ 1193-62-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 21, p. 5796 - 5800
  • 9
  • [ 7697-37-2 ]
  • [ 108-24-7 ]
  • [ 634-97-9 ]
  • [ 5919-26-6 ]
  • [ 13138-72-2 ]
  • [ 5930-93-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 1167
  • 10
  • [ 616-38-6 ]
  • [ 634-97-9 ]
  • [ 37619-24-2 ]
Reference: [1] Organic Process Research and Development, 2009, vol. 13, # 6, p. 1199 - 1201
  • 11
  • [ 634-97-9 ]
  • [ 37619-24-2 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 4458,4462
  • 12
  • [ 7697-37-2 ]
  • [ 108-24-7 ]
  • [ 634-97-9 ]
  • [ 5919-26-6 ]
  • [ 13138-72-2 ]
  • [ 5930-93-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 1167
  • 13
  • [ 634-97-9 ]
  • [ 43041-12-9 ]
Reference: [1] Canadian Journal of Chemistry, 2002, vol. 80, # 12, p. 1662 - 1667
  • 14
  • [ 634-97-9 ]
  • [ 1197-13-3 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 14, p. 2589 - 2592
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 20, p. 2997 - 3003
  • 15
  • [ 634-97-9 ]
  • [ 72908-87-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 2, p. 246 - 256
[2] Tetrahedron Letters, 1995, vol. 36, # 3, p. 413 - 416
[3] Australian Journal of Chemistry, 1990, vol. 43, # 2, p. 355 - 365
  • 16
  • [ 634-97-9 ]
  • [ 4043-88-3 ]
Reference: [1] Synthetic Communications, 1980, vol. 10, # 7, p. 529 - 540
  • 17
  • [ 634-97-9 ]
  • [ 263382-27-0 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 14, p. 2589 - 2592
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