[ CAS No. 1253799-29-9 ] {[proInfo.proName]}

Name: 1253799-29-9|Phenyl 2-(benzyloxy)-3-(dibenzylamino)-5-fluoro-6-methylbenzoate|97%
Brand: Ambeed
SKU: A136576
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Quality Control of [ 1253799-29-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1253799-29-9 ]

SDS Specification

Alternatived Products of [ 1253799-29-9 ]

Product Details of [ 1253799-29-9 ]

CAS No. :	1253799-29-9	MDL No. :	MFCD28142365
Formula :	C₃₅H₃₀FNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VRXGVVAMXZXKNA-UHFFFAOYSA-N
M.W :	531.62	Pubchem ID :	71739305
Synonyms :

Calculated chemistry of [ 1253799-29-9 ]

Physicochemical Properties

Num. heavy atoms :	40
Num. arom. heavy atoms :	30
Fraction Csp3 :	0.11
Num. rotatable bonds :	11
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	156.93
TPSA :	38.77 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.73
Log Po/w (XLOGP3) :	8.37
Log Po/w (WLOGP) :	8.1
Log Po/w (MLOGP) :	6.64
Log Po/w (SILICOS-IT) :	7.97
Consensus Log Po/w :	7.16

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-8.24
Solubility :	0.00000307 mg/ml ; 0.0000000058 mol/l
Class :	Poorly soluble
Log S (Ali) :	-9.05
Solubility :	0.000000473 mg/ml ; 0.0000000009 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-12.9
Solubility :	0.0000000001 mg/ml ; 0.0 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	3.88

Safety of [ 1253799-29-9 ]

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 [ 1253799-29-9 ]

* 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 [ 1253799-29-9 ]
Downstream synthetic route of [ 1253799-29-9 ]

[ 1253799-29-9 ] Synthesis Path-Upstream 1~8

1
[ 1207284-89-6 ]
[ 100-39-0 ]
[ 1253799-29-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 100℃; for 18 h; Inert atmosphere Stage #2: With triethylamine In 1-methyl-pyrrolidin-2-one; water at 8℃; for 0.166667 h; Inert atmosphere	To a solution of 500 g of compound 66 in 4.25 L N-methylpyrolidinone was added N,N-diisopropyIethylamine (620 ml) followed by BnBr (425 mL, 2.5 equiv.). The mixture was heated at 100 ⁰C for 18 h then cooled to 8 ⁰C and treated over 10 min with 25percent w/w aqueous triethyl amine aqueous. The mixture was allowed to stir for 25 minutes at ambient temperature before being cooled to 15 ⁰C adding water (10 L) over ca. 3 hours to precipitate product. The obtained pale colored suspension was filtered then washed with 2 L water and dried. The crude product (750 g) was then dissolved in 4.1 L toluene and filtered through silica gel to give 762 g of a yellow solid that was recrystallized from acetone/heptane to afford 606 g of desired compound 67 (80percent yield) obtained as an off-white solid: ¹H NMR (400 MHz, CDCl₃) δ 7.48-7.03 (m, 20 H), 6.60 (d, J= 1 1.5 Hz, 1 H), 5.31 (s, 2H), 4.33 (s, 4 H), 2.30 (s, 3H).

Reference： [1] Patent: WO2010/126607, 2010, A2, . Location in patent: Page/Page column 172/251

2
[ 220901-72-4 ]
[ 1253799-29-9 ]

Reference： [1] Patent: WO2010/126607, 2010, A2,

3
[ 1207283-54-2 ]
[ 1253799-29-9 ]

Reference： [1] Patent: WO2010/126607, 2010, A2,

4
[ 1207283-55-3 ]
[ 1253799-29-9 ]

Reference： [1] Patent: WO2010/126607, 2010, A2,

5
[ 1207284-87-4 ]
[ 1253799-29-9 ]

Reference： [1] Patent: WO2010/126607, 2010, A2,

6
[ 1207284-88-5 ]
[ 1253799-29-9 ]

Reference： [1] Patent: WO2010/126607, 2010, A2,

7
[ 394-04-7 ]
[ 1253799-29-9 ]

Reference： [1] Patent: WO2010/126607, 2010, A2,

8
[ 100-39-0 ]
[ 1253799-29-9 ]

Reference： [1] Patent: WO2010/126607, 2010, A2,

[ 1253799-29-9 ] Synthesis Path-Downstream 1~14

1
[ 1207284-89-6 ]
[ 100-39-0 ]
[ 1253799-29-9 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a solution of 500 g of compound 66 in 4.25 L N-methylpyrolidinone was added N,N-diisopropyIethylamine (620 ml) followed by BnBr (425 mL, 2.5 equiv.). The mixture was heated at 100 0C for 18 h then cooled to 8 0C and treated over 10 min with 25% w/w aqueous triethyl amine aqueous. The mixture was allowed to stir for 25 minutes at ambient temperature before being cooled to 15 0C adding water (10 L) over ca. 3 hours to precipitate product. The obtained pale colored suspension was filtered then washed with 2 L water and dried. The crude product (750 g) was then dissolved in 4.1 L toluene and filtered through silica gel to give 762 g of a yellow solid that was recrystallized from acetone/heptane to afford 606 g of desired compound 67 (80% yield) obtained as an off-white solid: 1H NMR (400 MHz, CDCl3) delta 7.48-7.03 (m, 20 H), 6.60 (d, J= 1 1.5 Hz, 1 H), 5.31 (s, 2H), 4.33 (s, 4 H), 2.30 (s, 3H).

Reference： [1]Patent: WO2010/126607,2010,A2 .Location in patent: Page/Page column 172/251

2
[ 1253799-29-9 ]
[ 1253799-28-8 ]
[ 1253799-30-2 ]

Yield	Reaction Conditions	Operation in experiment
62%		To a solution of lithium diisopropylamide (2.0 M in hexanes, 478 muL, 0.959 mmol, 2 equiv) and TMEDA (144 muL, 0.957 mmol, 2 equiv) in THF (8 mL) at -78 0C was added a solution of compound 67 (509 mg, 0.957 mmol, 2 equiv) in THF (2 mL) by dropwise addition. This resulted in a dark red colored solution. After 10 min, a solution of enone 59 (235 mg, 0.473 mmol, 1 equiv) in THF (1 mL) was added, followed by slow addition of LHMDS (1 M in hexanes; 957 muL, 0.957 mmol, 2 equiv). The reaction mixture was allowed to warm to -15 0C over 80 min. Excess base was quenched by the addition of a saturated, aqueous solution of ammonium chloride (1 mL). The solution was warmed to ambient temperature, poured into a saturated, aqueous solution of ammonium chloride (15 mL) and water (5 mL) and extracted with EtOAc (2 x 25 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification of the resulting oil via flash column chromatography on silica gel (Silicycle, 40 g, 5 to 12.5% EtOAc in hexanes gradient) provided 7-fluoro-9-dibenzyl analog 68 as a yellow oil (275 mg, 62%): 1H NMR (400 MHz, CDCl3) delta 16.59 (s, 1 H), 7.53-7.44 (m, 4 H), 7.41-7.20 (m, 12 H), 7.18-7.10 (m, 4 H), 6.65 (d, J= 10.4 Hz, 1 H), 5.38 (d, J= 9.8 Hz, 1 H), 5.36 (s, 2 H), 5.07 (d, J= 9.8 Hz, 1 H), 4.36 (d, J= 14.0 Hz, 2 H), 4.21 (d, J= 14.0 Hz, 2 H), 4.04 (d, J= 9.8 Hz, 1 H), 2.89 (d, J= 15.9 Hz, 1 H), 2.66 (d, J= 15.0 Hz, 1 H), 2.48 (s, 6 H), 2.32-2.22 (m, 1 H), 2.15 (dd, J = 4.9, 12.7 Hz, 1 H), 1.08 (s, 9 H), 0.25 (s, 3 H), 0.18 (s, 3 H); MS (ESI) m/z 934.40 (M+H).

Reference： [1]Patent: WO2010/126607,2010,A2 .Location in patent: Page/Page column 173/251-174/251

3
[ 1253799-29-9 ]
(4S,4aS,5aR,12aS)-9-amino-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide [ No CAS ]

Reference： [1]Organic Process Research and Development,2013,vol. 17,p. 838 - 845

4
[ 1253799-29-9 ]
[ 1207283-85-9 ]

Reference： [1]Organic Process Research and Development,2013,vol. 17,p. 838 - 845

5
[ 1253799-29-9 ]
(4S,4aS,5aR,12aS)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[2-(pyrrolidin-1-yl)acetamido]-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide dihydrochloride [ No CAS ]

Reference： [1]Organic Process Research and Development,2013,vol. 17,p. 838 - 845

6
[ 1253799-29-9 ]
C₄₉H₄₄FN₃O₇ [ No CAS ]

Reference： [1]Organic Process Research and Development,2013,vol. 17,p. 838 - 845

7
[ 852821-06-8 ]
[ 1253799-29-9 ]
C₅₅H₅₈FN₃O₇Si [ No CAS ]