Home Cart 0 Sign in  
X

[ CAS No. 7781-10-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 7781-10-4
Chemical Structure| 7781-10-4
Chemical Structure| 7781-10-4
Structure of 7781-10-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 7781-10-4 ]

Related Doc. of [ 7781-10-4 ]

Alternatived Products of [ 7781-10-4 ]

Product Details of [ 7781-10-4 ]

CAS No. :7781-10-4 MDL No. :MFCD00619245
Formula : C7H6ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :BJGDLOLPALCTJQ-UHFFFAOYSA-N
M.W : 167.60 Pubchem ID :265829
Synonyms :

Calculated chemistry of [ 7781-10-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.8
TPSA : 30.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.62
Log Po/w (MLOGP) : 1.11
Log Po/w (SILICOS-IT) : 1.58
Consensus Log Po/w : 1.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.555 mg/ml ; 0.00331 mol/l
Class : Soluble
Log S (Ali) : -1.84
Solubility : 2.45 mg/ml ; 0.0146 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.328 mg/ml ; 0.00195 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 7781-10-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7781-10-4 ]

* 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 [ 7781-10-4 ]
  • Downstream synthetic route of [ 7781-10-4 ]

[ 7781-10-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 3680-69-1 ]
  • [ 74-88-4 ]
  • [ 7781-10-4 ]
YieldReaction ConditionsOperation in experiment
94% With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 1 h; lodomethane (12.2 mL, 195 MMOL) was added to a solution of 4-Chloro-7H- pyrrolo [2,3-d] pyrimidine (15.0 g, 97.7 MMOL) and cesium carbonate (47.7 g, 146.5 MMOL) IN DMF (200 mL). The reaction mixture was stirred at room temperature 1 h, quenched with H20 (500 mL), and extracted with EtOAc (3X200ML). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash column chromatography (silica, 2: 8X3 : 7 EtOAc: hexanes) provided the title compound as an off-white solid (15.4 g, 94percent). MS: 168.5 (MH+) ; HPLC Rf : 3.45 min. (HPLC method 4); HPLC purity: 96percent.
83%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 0.333333 h;
Stage #2: at 0 - 20℃; for 4 h;
Step 1 : To a stirred solution of 4-chloro-7/-/-pyrrolo[2,3-d]pyrimidine (4 g, 26.143 mmol) in THF (40 mL) was added potassium tertiary butoxide (3.8 g, 33.986 mmol, 1.3 equiv) at 0°C. The reaction mixture was allowed to stir at room temperature for 20 min. Methyl iodide (2.4 mL, 39.215 mol, 1.5 equiv) was added at 0°C to the reaction mixture and stirred for 4h at room temperature. The solvent was evaporated, diluted with ice water (50 mL) and the precipitated solid was filtered & dried in vacuo to give 4-chloro-7-methyl- 7H-pyrrolo[2,3-d]pyrimidine as off white solid (3.6 g, 83 percent). LCMS (ES) m/z = 168.1 [M+H]+. H NMR (400 MHz, DMSO-d6) δ ppm 3.84 (s, 3H), 6.62 (d, J = 3.2 Hz, 1 H), 7.72 (d, J = 3.2 Hz, 1 H), 8.62 (s, 1 H).
81% With caesium carbonate In 1-methyl-pyrrolidin-2-one at 15 - 23℃; for 4.5 h; Add Cs2CO3(845 g, 2.60 mol) at 15 °C to a solution of 4-chloro-7H-pyrrolo[2,3- d]pyrimidine (200 g, 1.29 mol) in N-methyl-2-pyrrolidone (1.20 L). Warm to 23 °C, add Mel (202 g, 1.43 mol) dropwise over 30 min, and stir for 4 h. After this time, pour onto ice-water (2.00 L) and stir for 30 min. Filter, then slurry material in H20 (1.00 L). Filter and dry to give the title compound (180 g, 81percent). ES/MS m/z (35C1) 168.0 (M+H).
Reference: [1] Patent: WO2004/56830, 2004, A1, . Location in patent: Page 93
[2] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 16, p. 2153 - 2157
[3] Patent: WO2017/46739, 2017, A1, . Location in patent: Page/Page column 89
[4] Patent: WO2018/194885, 2018, A1, . Location in patent: Page/Page column 15
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7193 - 7207
[6] Chemische Berichte, 1981, vol. 114, # 6, p. 2056 - 2063
[7] Patent: WO2011/119663, 2011, A1, . Location in patent: Page/Page column 81-82
[8] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 18, p. 5473 - 5482
[9] MedChemComm, 2014, vol. 5, # 10, p. 1500 - 1506
[10] Patent: WO2017/212012, 2017, A1, . Location in patent: Page/Page column 33; 34
[11] Patent: TW2018/2094, 2018, A, . Location in patent: Page/Page column 47; 77; 115
  • 2
  • [ 74-88-4 ]
  • [ 7781-10-4 ]
Reference: [1] Patent: WO2005/95357, 2005, A2, . Location in patent: Page/Page column 177; 178
  • 3
  • [ 81965-21-1 ]
  • [ 7781-10-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3199 - 3203
  • 4
  • [ 74-88-4 ]
  • [ 7781-10-4 ]
Reference: [1] Patent: WO2004/7479, 2004, A1, . Location in patent: Page 34
  • 5
  • [ 3680-71-5 ]
  • [ 7781-10-4 ]
Reference: [1] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 16, p. 2153 - 2157
  • 6
  • [ 7781-10-4 ]
  • [ 1266343-30-9 ]
YieldReaction ConditionsOperation in experiment
93% With N-Bromosuccinimide In dichloromethane at 0 - 25℃; for 2 h; Example 1 5-(1H-1,3-Benzodiazol-2-yl)-7-methyl-N-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine[0122]STEP 1: 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine [Chem. 3]To a stirred solution of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (WO2005/095357, 6.02 g, 35.9 mmol) in dichloromethane (120 mL) was added N-bromosuccinimide (7.67 g, 43.1 mmol) at 0 oC. The resulting mixture was stirred at room temperature for 2 hrs. The reaction mixture was quenched with saturated sodium bicarbonate aqueous solution (200 mL), and extracted with dichloromethane (200 mL). The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (dichloromethane/ethyl acetate=10/1) to give the title compound (8.27 g, 93percent) as a white solid.;LCMS (Method A) m/z: M+1 247.9; tR = 2.70 min.
86% With N-Bromosuccinimide In dichloromethane at 15 - 23℃; for 3 h; Add N-bromosuccinimide (418 g, 2.35 mol) portionwise over 20 min at 15 °C to a solution of 4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (355 g, 2.12 mol) indichloromethane (3.19 L), and stir at 23 °C for 3 h. After this time, filter, wash with H20 (5.32 L), and dry to give the title compound (448 g, 86percent) as a white solid. ES/MS m/z (35C1,79Br) 245.9 (M+H).
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7193 - 7207
[2] Patent: WO2011/18894, 2011, A1, . Location in patent: Page/Page column 25-26
[3] Patent: WO2018/194885, 2018, A1, . Location in patent: Page/Page column 16
[4] Patent: WO2011/119663, 2011, A1, . Location in patent: Page/Page column 82
[5] MedChemComm, 2014, vol. 5, # 10, p. 1500 - 1506
  • 7
  • [ 7781-10-4 ]
  • [ 1337531-36-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7193 - 7207
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 7781-10-4 ]

Chlorides

Chemical Structure| 3680-69-1

[ 3680-69-1 ]

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.96

Chemical Structure| 16019-34-4

[ 16019-34-4 ]

7-Benzyl-4-chloro-7H-pyrrolo[2,3-d] pyrimidine

Similarity: 0.93

Chemical Structure| 90213-67-5

[ 90213-67-5 ]

2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.91

Chemical Structure| 84955-31-7

[ 84955-31-7 ]

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Similarity: 0.87

Chemical Structure| 90213-66-4

[ 90213-66-4 ]

2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.87

Related Parent Nucleus of
[ 7781-10-4 ]

Other Aromatic Heterocycles

Chemical Structure| 3680-69-1

[ 3680-69-1 ]

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.96

Chemical Structure| 16019-34-4

[ 16019-34-4 ]

7-Benzyl-4-chloro-7H-pyrrolo[2,3-d] pyrimidine

Similarity: 0.93

Chemical Structure| 90213-67-5

[ 90213-67-5 ]

2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.91

Chemical Structure| 84955-31-7

[ 84955-31-7 ]

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Similarity: 0.87

Chemical Structure| 90213-66-4

[ 90213-66-4 ]

2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.87