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[ CAS No. 369-35-7 ] {[proInfo.proName]}

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Chemical Structure| 369-35-7
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Flavio S.P. Cardoso ; Appasaheb L. Kadam ; Ryan C. Nelson , et al. DOI: PubMed ID:

Abstract: A low-cost, protecting group-free route to 6-(2-fluoro-4-nitrophenyl)-2-oxa-6-azaspiro[3.3]heptane (1), the starting material for the in-development tuberculosis treatment TBI-223, is described. The key bond forming step in this route is the creation of the azetidine ring through a hydroxide-facilitated alkylation of 2-fluoro-4-nitroaniline (2) with 3,3-bis(bromomethyl)oxetane (BBMO, 3). After optimization, this ring formation reaction was demonstrated at 100 g scale with isolated yield of 87% and final product purity of >99%. The alkylating agent 3 was synthesized using an optimized procedure that starts from tribromoneopentyl alcohol (TBNPA, 4), a commercially available flame retardant. Treatment of 4 with sodium hydroxide under Schotten–Baumann conditions closed the oxetane ring, and after distillation, 3 was recovered in 72% yield and >95% purity. This new approach to compound 1 avoids the previous drawbacks associated with the synthesis of 2-oxa-6-azaspiro[3,3]heptane (5), the major cost driver used in previous routes to TBI-223. The optimization and multigram scale-up results for this new route are reported herein.

Keywords: tuberculosis ; TBI-223 ; azaspiro[3.3]heptane ; spiroamine

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Product Details of [ 369-35-7 ]

CAS No. :369-35-7 MDL No. :MFCD00034560
Formula : C6H5FN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LETNCFZQCNCACQ-UHFFFAOYSA-N
M.W : 156.12 Pubchem ID :101254
Synonyms :

Calculated chemistry of [ 369-35-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.63
TPSA : 71.84 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) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : -0.59
Consensus Log Po/w : 0.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.95
Solubility : 1.77 mg/ml ; 0.0113 mol/l
Class : Very soluble
Log S (Ali) : -2.38
Solubility : 0.654 mg/ml ; 0.00419 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.69
Solubility : 3.22 mg/ml ; 0.0207 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 369-35-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 369-35-7 ]

* 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 [ 369-35-7 ]
  • Downstream synthetic route of [ 369-35-7 ]

[ 369-35-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 402-67-5 ]
  • [ 364-78-3 ]
  • [ 17809-36-8 ]
  • [ 369-35-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 2, p. 442 - 443
[2] Journal of Organic Chemistry, 1996, vol. 61, # 9, p. 2934 - 2935
[3] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1437 - 1444
  • 2
  • [ 402-67-5 ]
  • [ 364-78-3 ]
  • [ 17809-36-8 ]
  • [ 369-35-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 2, p. 442 - 443
[2] Journal of Organic Chemistry, 1996, vol. 61, # 9, p. 2934 - 2935
[3] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1437 - 1444
  • 3
  • [ 399-31-5 ]
  • [ 17809-36-8 ]
  • [ 369-35-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4476 - 4487
[2] Journal of Fluorine Chemistry, 1989, vol. 42, p. 245 - 256
  • 4
  • [ 402-67-5 ]
  • [ 369-35-7 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 15, p. 4878 - 4888
[2] Journal of Organic Chemistry, 1986, vol. 51, # 25, p. 5039 - 5040
[3] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 6, p. 1513 - 1520
  • 5
  • [ 348-19-6 ]
  • [ 369-35-7 ]
Reference: [1] Organic Preparations and Procedures International, 2003, vol. 35, # 4, p. 422 - 425
[2] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 88,89
[3] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 6, p. 1513 - 1520
  • 6
  • [ 369-34-6 ]
  • [ 369-35-7 ]
Reference: [1] Patent: US2436100, 1944, ,
[2] Patent: US2391179, 1942, ,
[3] Patent: US5310723, 1994, A,
  • 7
  • [ 402-67-5 ]
  • [ 364-78-3 ]
  • [ 17809-36-8 ]
  • [ 369-35-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 2, p. 442 - 443
[2] Journal of Organic Chemistry, 1996, vol. 61, # 9, p. 2934 - 2935
[3] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1437 - 1444
  • 8
  • [ 399-31-5 ]
  • [ 17809-36-8 ]
  • [ 369-35-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4476 - 4487
[2] Journal of Fluorine Chemistry, 1989, vol. 42, p. 245 - 256
  • 9
  • [ 399-31-5 ]
  • [ 369-35-7 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1976, vol. 30, p. 141 - 149
[2] Organic Preparations and Procedures International, 2003, vol. 35, # 4, p. 422 - 425
[3] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 6, p. 1513 - 1520
[4] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 88,89
[5] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 88,89
[6] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 88,89
  • 10
  • [ 348-54-9 ]
  • [ 369-35-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 6, p. 1513 - 1520
[2] Journal of Fluorine Chemistry, 1989, vol. 42, p. 245 - 256
  • 11
  • [ 367-11-3 ]
  • [ 369-35-7 ]
Reference: [1] Patent: US2436100, 1944, ,
[2] Patent: US2391179, 1942, ,
  • 12
  • [ 369-34-6 ]
  • [ 369-35-7 ]
Reference: [1] Patent: US2436100, 1944, ,
[2] Patent: US2391179, 1942, ,
  • 13
  • [ 369-35-7 ]
  • [ 819057-45-9 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 1979 - 1988
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