[ CAS No. 139180-30-6 ] {[proInfo.proName]}

Name: 139180-30-6|4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol|99%
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SKU: A132647
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Quality Control of [ 139180-30-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 139180-30-6 ]

SDS Specification

Alternatived Products of [ 139180-30-6 ]

Product Details of [ 139180-30-6 ]

CAS No. :	139180-30-6	MDL No. :	MFCD00908394
Formula :	C₁₆H₁₅N₇O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PWTBZOIUWZOPFT-UHFFFAOYSA-N
M.W :	337.34	Pubchem ID :	176407
Synonyms :		Chemical Name :	4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol

Calculated chemistry of [ 139180-30-6 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	20
Fraction Csp3 :	0.12
Num. rotatable bonds :	5
Num. H-bond acceptors :	6.0
Num. H-bond donors :	3.0
Molar Refractivity :	91.31
TPSA :	127.39 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	2.2
Log Po/w (WLOGP) :	1.54
Log Po/w (MLOGP) :	0.89
Log Po/w (SILICOS-IT) :	0.44
Consensus Log Po/w :	1.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.58
Solubility :	0.0888 mg/ml ; 0.000263 mol/l
Class :	Soluble
Log S (Ali) :	-4.51
Solubility :	0.0104 mg/ml ; 0.000031 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.11
Solubility :	0.0026 mg/ml ; 0.00000771 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.88

Safety of [ 139180-30-6 ]

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

Application In Synthesis of [ 139180-30-6 ]

* 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 [ 139180-30-6 ]
Downstream synthetic route of [ 139180-30-6 ]

[ 139180-30-6 ] Synthesis Path-Upstream 1~7

1
[ 51-67-2 ]
[ 139181-28-5 ]
[ 139180-30-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	at 20℃;	Tyramine (490 mg, 3.75 mmol) was added to a suspension of 2-(furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine (18) (250 mg, 892 µmol) in acetonitrile (25 mL). The reaction mixture was stirred overnight at room temperature. After 22 h the solvent was evaporated, the residue was adsorbed on Celite and purified by column chromatography (dichloromethane: methanol 25:75). The collected fractions with product were evaporated to dryness and recrystallised from ethyl acetate. The title compound 5 (100 mg, 33percent) was obtained as a white solid, mp: 229-231 °C (lit.⁶ 225-227 °C). ¹H NMR (400 MHz, d₆-DMSO, 353 K) δ 8.91 (s, 1H), 7.92 (br s, 2H), 7.79 (m, 1H), 7.14 (br t, 1H), 7.04 (m, 3H), 6.71 (m, 2H), 6.64 (dd, J = 3.3, 1.8 Hz, 1H), 3.49 (m, 2H), 2.78 (m, 2H). ¹³C NMR (101 MHz, d₆-DMSO) δ 161.1 (C), 159.0 (C), 155.9 (C), 155.4 (C), 150.1 (C), 146.1 (C), 144.1 (CH), 129.1 (CH), 115.0 (CH), 111.4 (CH), 111.2 (CH), 42.4 (CH₂), 33.9 (CH₂). HRMS (C₁₆H₁₅N₇O₂): calc’d 338.1360 [M+H]⁺, found 338.1353. HPLC: t_R 7.34 min, 98percent (214 nm), 97percent (254 nm).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3427 - 3433
[2] Structural Chemistry, 2013, vol. 24, # 4, p. 1241 - 1251
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 2, p. 718 - 738
[4] Molecular Pharmacology, 1995, vol. 48, # 6, p. 970 - 974
[5] Patent: US5270311, 1993, A,
[6] Patent: US5356894, 1994, A,
[7] Patent: US5246932, 1993, A,

2
[ 6053-32-3 ]
[ 139180-30-6 ]

3
[ 3663-61-4 ]
[ 139180-30-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3427 - 3433
[2] Structural Chemistry, 2013, vol. 24, # 4, p. 1241 - 1251
[3] Patent: US5246932, 1993, A,

4
[ 3326-71-4 ]
[ 139180-30-6 ]

5
[ 139181-27-4 ]
[ 139180-30-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3427 - 3433
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 2, p. 718 - 738

6
[ 617-90-3 ]
[ 139180-30-6 ]

Reference： [1] Patent: US5246932, 1993, A,

7
[ 114953-87-6 ]
[ 139180-30-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 2, p. 718 - 738

[ 139180-30-6 ] Synthesis Path-Downstream 1~21

1
[ 51-67-2 ]
[ 139181-28-5 ]
[ 139180-30-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	In acetonitrile; at 20℃;	Tyramine (490 mg, 3.75 mmol) was added to a suspension of 2-(furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine (18) (250 mg, 892 mumol) in acetonitrile (25 mL). The reaction mixture was stirred overnight at room temperature. After 22 h the solvent was evaporated, the residue was adsorbed on Celite and purified by column chromatography (dichloromethane: methanol 25:75). The collected fractions with product were evaporated to dryness and recrystallised from ethyl acetate. The title compound 5 (100 mg, 33%) was obtained as a white solid, mp: 229-231 C (lit.6 225-227 C). 1H NMR (400 MHz, d6-DMSO, 353 K) delta 8.91 (s, 1H), 7.92 (br s, 2H), 7.79 (m, 1H), 7.14 (br t, 1H), 7.04 (m, 3H), 6.71 (m, 2H), 6.64 (dd, J = 3.3, 1.8 Hz, 1H), 3.49 (m, 2H), 2.78 (m, 2H). 13C NMR (101 MHz, d6-DMSO) delta 161.1 (C), 159.0 (C), 155.9 (C), 155.4 (C), 150.1 (C), 146.1 (C), 144.1 (CH), 129.1 (CH), 115.0 (CH), 111.4 (CH), 111.2 (CH), 42.4 (CH2), 33.9 (CH2). HRMS (C16H15N7O2): calc?d 338.1360 [M+H]+, found 338.1353. HPLC: tR 7.34 min, 98% (214 nm), 97% (254 nm).
	In acetonitrile;	Example 81 4-(2-Aminoethyl)phenol (2.74 g) was added to a stirred suspension of 7-amino-2-(2-furyl)-5-methylsulphonyl-[1,2,4]triazolo-[1,5-a][1,3,5]triazine (1.4 g) in acetonitrile (150 ml) and stirring was continued overnight. The solvent was evaporated and the residue was purified by chromatography on silica (100 g) eluding with dichloromethane containing methanol (50% v/v). The solid (1.23 g) obtained was crystallized from ethyl acetate to give 7-amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino-[1,2,4]-triazolo[1,5-a][1,3,5]triazine, m.p. 225-227 C.; microanalysis, found: C, 56.7; H, 4.6; N, 29.4%; C16 H15 N7 O2 requires C, 57.0; H, 4.5; N, 29.1%, NMR: 2.73(t, 2H, CH2 Ar), 3.41(t, 2H, NHCH), 6.66(complex, 3H, 2phenyl-H and furyl-4H), 7.02 (complex, 3H, 2phenyl-H and furyl-3H), 7.40(br t, 1H, -NH-), 7.82(q, 1H, furyl-5H), 8.0-8.4(br d, 2H, NH2) and 9.1(s, 1H, OH); m/e 333 (M+H)+.
	In acetonitrile;	EXAMPLE 81 4-(2-Aminoethyl)phenol (2.74 g) was added to a stirred suspension of 7-amino-2-(2-furyl)-5-methylsulphonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine (1.4 g) in acetonitrile (150 ml) and stirring was continued overnight. The solvent was evaporated and the residue was purified by chromatography on silica (100 g) eluding with dichloromethane containing methanol (50% v/v). The solid (1.23 g) obtained was crystallized from ethyl acetate to give 7-amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino-[1,2,4]-triazolo[1,5-a][1,3,5]triazine, m.p. 225-227 C.; microanalysis, found: C, 56.7; H, 4.6; N, 29.4%; C16 H15 N7 O2 requires C, 57.0; H, 4.5; N, 29.1%, NMR: 2.73(t, 2H, CH2 Ar), 3.41(t, 2H, NHCH2), 6.66(complex, 3H, 2phenyl-H and furyl-4H), 7.02(complex, 3H, 2phenyl-H and furyl-3H), 7.40(br t, 1H, --NH--), 7.82(q, 1H, furyl-5H), 8.0-8.4(br d, 2H, NH2) and 9.1(s, 1H, OH); m/e 333 (M+H)+.

In acetonitrile;

(4) 4-(2-Aminoethyl)phenol (2.74 g) was added to a stirred suspension of 7-amino-2-(2-furyl)-5-methylsulphonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine (1.4 g) in acetonitrile (150 ml) and stirring was continued overnight. The solvent was evaporated and the residue was purified by chromatography on silica (100 g) eluding with dichloromethane containing methanol (50% v/v). The solid (1.23 g) obtained was crystallized from ethyl acetate to give 7-amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino-[1,2,4]triazolo[1,5-a][1,3,5]triazine, m.p. 225-227 C.; microanalysis, found: C, 56.7; H, 4.6; N, 29.4%; C16 H15 N7 O2 requires C, 57.0; H, 4.5; N, 29.1%, NMR: 2.73(t, 2H, CH2 Ar), 3.41(t, 2H, NHCH2), 6.66(complex, 3H, 2 phenyl-H and furyl-4H), 7.02(complex, 3H, 2 phenyl-H and furyl-3H), 7.40(br t, 1H, --NH--), 7.82(q, 1H, furyl-5H), 8.0-8.4(br d, 2H, NH2) and 9.1(s, 1H, OH); m/e 333 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3427 - 3433
[2]Structural Chemistry,2013,vol. 24,p. 1241 - 1251
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 718 - 738
[4]Molecular Pharmacology,1995,vol. 48,p. 970 - 974
[5]Patent: US5270311,1993,A
[6]Patent: US5356894,1994,A
[7]Patent: US5246932,1993,A

2
[ 139180-30-6 ]
[125I]-2-iodo-4-(2-[7-amino-2-{2-furyl}{1,2,4}triazolo{2,3-a}{1,3,5}triazin-5-yl-amino]ethyl)phenol [ No CAS ]

Reference： [1]Molecular Pharmacology,1995,vol. 48,p. 970 - 974

3
[ 139180-30-6 ]
7-aminomethyl-octahydro-pyrido[1,2-<i>a</i>]pyrazine-2-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
(7RS,9aSR)-7-[(7-amino-2-furan-2-yl[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)methyl]octahydropyrido[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6218 - 6229

4
[ 139180-30-6 ]
C₁₆H₁₄⁽¹³¹⁾IN₇O₂ [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2003,vol. 46,p. S372 - S372

5
[ 6674-22-2 ]
[ 139181-28-5 ]
[ 139180-30-6 ]
[ 146229-41-6 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	EXAMPLE 1 7-amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine (0.91 g) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 0.37 ml) were added to a suspension of 7-amino-2-(2-furyl)-5-methylsulphonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine (0.82 g) in acetonitrile (50 ml) and the resulting mixture was heated under reflux for 17 hours, after which time thin layer chromatography (TLC) analysis on silica plates (eluent: methylene chloride-methanol 19:1 v/v) indicated that no methanesulphonyl starting material remained. The solvent was then evaporated and the residue was purified by column chromatography on silica (75 g) eluding with ethyl acetate-methylene chloride 7:3 v/v. A white solid was obtained, and this was crystallized from isopropanol to afford 7-amino-5-[4-(2-[7-amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino]ethyl)phenoxy]-2-(2-furyl)[ 1,2,4]triazolo[1,5-a][1,3,5]triazine, m.p. 285-289 C.; microanalysis, found: C, 54.1; H, 4.4; N, 30.8%; C24 H19 N13 O3 1.0(C3 H7 OH) requires: C, 54.2; H, 4.5; N, 30.5%; NMR: 2.92 (t, 2H, phenyl-CH2), 3.55 (q, 2H, CH2-N), 6.67 (m, 2H, 2 furyl-4H), 7.0 (d, 1H, furyl-3H), 7.11 (d, 1H, furyl-3'H), 7.16 and 7.35 (A2 B2 pattern, 4H, phenyl-H), 7.5 (br t, 1H, NH rotamers), 7.85 (d, 1H, furyl-5H), 7.89 (d, 1H, furyl-5'H), 8.12 (br s, 2H, NH2) and 8.93 (d, 2H, NH2); m/e (M+H)+ 538. The necessary starting material was prepared as follows:

Reference： [1]Patent: US5246932,1993,A

6
[ 3282-30-2 ]
[ 139180-30-6 ]
[ 139180-31-7 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; isopropyl alcohol;	EXAMPLE 82 7-Amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine (1 g, prepared as described in Example 81) was suspended in dichloromethane (20 ml) and trifluoroacetic acid (20 ml) was added with stirring. Pivaloyl chloride (0.4 ml) was added dropwise at ambient temperature. The mixture was stirred for 2 hours and then the dichloromethane and trifluoroacetic acid was removed in vacuo. The residue was purified by chromatography on silica (100 g) eluding with dichloromethane containing methanol (5.0% v/v). The solid obtained (1.2 g) was crystallized from toluene and finally from isopropanol (25 ml) to give 7-amino-2-(2-furyl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine as a solid; m.p. 208-210 C.; microanalysis, found: C, 59.6; H, 6.1; N, 21.7%; C21 H24 N7 O3 0.5 C3 H7 OH requires C, 59.9; H, 6.0; N, 21.7%; NMR 1.06(d, ca 3H, (CH3)2 CHOH), 1.3(s, 9H, CH3 C), 2.9(t, 2H, CH2 Ar), 3.55 (t, 2H, CH2 N), 3.80(heptet, ca 0.5 H, (CH3)2 CHOH), 6.68(dd, 1H, furyl-4H), 7.01 and 7.30 (A2 B2 pattern, 4H, phenyl-H), 7.08 (d, 1H, furyl-3H) and 7.82(d, 1H, furyl-5H); m/e 422 (M+H)+.

Reference： [1]Patent: US5356894,1994,A

7
[ 6053-32-3 ]
[ 139180-30-6 ]

8
[ 3663-61-4 ]
[ 139180-30-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3427 - 3433
[2]Structural Chemistry,2013,vol. 24,p. 1241 - 1251
[3]Patent: US5246932,1993,A

9
[ 139181-27-4 ]
[ 139180-30-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3427 - 3433
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 718 - 738

10
[ 2969-81-5 ]
[ 139180-30-6 ]
[ 1436428-60-2 ]
[ 1436428-61-3 ]
[ 1436428-62-4 ]

Yield	Reaction Conditions	Operation in experiment
5%; 6%; 13%	With potassium carbonate; In acetone; at 20 - 50℃; for 48h;	4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl) phenol (5) (50.0 mg, 148 mumol) was suspended in acetone (4 mL) and potassium carbonate (20.5 mg, 148 mumol) and ethyl 4-bromobutyrate (21.5 muL, 148 mumol) was added at room temperature. The reaction mixture was heated up to 50 C for 5 h, then another batch of potassium carbonate (20.5 mg, 148 mumol) and ethyl 4-bromobutyrate (21.5 muL, 148 mumol) was added. The reaction mixture was stirred at 50 C for another 43 h. Then the solvent was removed under vacuum and the crude material was purified by column chromatography (dichloromethane 100% ? dichloromethane: ethanol 95:5). The title compound 43 was obtained as a white solid (3.3 mg, 5%). Side product 44 was obtained as a white solid (4.1 mg, 6%). Side product 45 was obtained as a white solid (8.5 mg, 13%). 1H NMR (400 MHz, d6-DMSO) delta 8.50 - 8.00 (2 br s, ratio 1:5, 2H), 7.86 (s, 1H), 7.54 - 7.39 (2 br t, J = 5.7 Hz, ratio 1:2, 1H), 7.15 (m, 2H), 7.05 (dd, J = 3.4, 0.8 Hz, 1H), 6.84 (m, 2H), 6.67 (m, 1H), 4.06 (q, J = 7.1 Hz, 2H), 3.95 (t, J = 6.4 Hz, 2H), 3.44 (m, 2H), 2.78 (m, 2H), 2.44 (t, J = 7.3 Hz, 2H), 1.95 (m, 2H), 1.17 (t, J = 7.1 Hz, 3H). LCMS: m/z (ESI 20 V) 452.1 (MH+, 100). Some of the 13C signal show up twice, the signal with lower intensity is marked with an asterisk (). 13C NMR (101 MHz, d6-DMSO) delta 173.0 (C), 162.0 (C), 161.6 (C), 159.7 (C), 157.3 (C), 156.3 (C), 151.1 (C), 150.5 (C), 146.66 (C), 145.1 (CH), 132.0 (C), 130.2 (CH), 130.1 (CH), 114.8 (CH), 112.4 (CH), 112.1 (CH), 66.8 (CH2), 60.3 (CH2), 43.5 (CH2), 42.9 (CH2), 34.8 (CH2*), 34.4 (CH2), 30.62 (CH2), 24.72 (CH2), 14.6 (CH3). LCMS: m/z (ESI 20 V) 452.1 (MH+, 100). HRMS (C22H25N7O4): calc?d. 452.2046 [M+H]+, found 452.2043. HPLC: tR 8.97 min, 98% (214 nm), >99% (254 nm).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3427 - 3433

11
[ 75-36-5 ]
[ 139180-30-6 ]
[ 1436428-63-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 20h;	4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl) phenol (5) (50.0 mg, 148 mumol) was suspended in dichloromethane (2 mL) and trifluoroacetic acid (2 mL) was added. Acetyl chloride (11.6 muL, 163 mumol) was drop wise added at room temperature. After 20 h more acetyl chloride (5.80 muL, 81.5 mumol) was added. Overall another two equivalents of acetic chloride was batch wise added over the next 24 h till the reaction was completed by LCMS. The solvent was removed under vacuum and the crude material was purified by column chromatography (dichloromethane 100% ? dichloromethane: methanol 95:5). The title compound 46 was obtained as a white solid (50.2 mg, 89%), mp: 216-218 C. 1H NMR (400 MHz, d6-DMSO) delta 8.74 - 8.05 (3 br s, ratio 1:1:5, 2H), 7.91 (s, 1H), 7.95 - 7.63 (2 br t, J = 5.4 Hz, ratio 1:2, 1H), 7.30 (m, 2H), 7.16 - 7.08 (m, 1H), 7.07 - 7.01 (m, 2H), 6.70 (m, 1H), 3.52 (d, J = 5.3 Hz, 2H), 2.88 (t, J = 7.1 Hz, 2H), 2.26 (s, 3H). Some of the 13C signal show up twice, the signal with lower intensity is marked with an asterisk (). 13C NMR (101 MHz, d6-DMSO) delta 169.2 (C), 161.0 (C), 161.7 (C), 158.5 (C), 158.4 (C), 154.7 (C), 150.5 (C), 149.9 (C), 148.8 (C), 145.5 (C), 137.0 (C), 136.8 (C), 129.6 (CH), 121.6 (CH), 112.4 (CH), 112.0 (CH) 112.0 (CH), 42.7 (CH2), 42.12 (CH2), 34.2 (CH2), 34.0 (CH2), 21.0 (CH3), 20.8 (CH3). LCMS: m/z (ESI 20 V) 380.1 (MH+, 100). HRMS (C18H17N7O3): calc?d 380.1466 [M+H]+, found 380.1481. HPLC: tR 8.43 min, ?99% (214 nm), ?99% (254 nm).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3427 - 3433

12
[ 2082-59-9 ]
[ 139180-30-6 ]
[ 1436428-64-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 6.5h;	4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl) phenol (5) (50.0 mg, 148 mumol) was suspended in dichloromethane (2 mL) and trifluoroacetic acid (2 mL) was added. Butyric anhydride (26.7 muL, 163 mumol) was drop wise added at room temperature. After 2.5 h another equivalent of butyric anhydride (33.8 muL, 163 mumol) was drop wise added to the reaction mixture. After 4 h reaction time the solvent was removed under vacuum. The crude material was purified by column chromatography (dichloromethane 100% ? dichloromethane: methanol 95:5). The title compound 47 was obtained as a white solid (56.0 mg, 92%), mp: 223-225 C. 1H NMR (400 MHz, d6-DMSO) delta 8.52 - 8.00 (2 br s, ratio 1:5, 2H), 7.87 (s, 1H), 7.63 - 7.45 (2 br t, J = 5.4 Hz, ratio 1:2, 1H), 7.29 (m, 2H), 7.06 (m, 3H), 6.68 (m, 1H), 3.50 (m, 2H), 2.88 (m, 2H), 2.54 (t, J = 7.3 Hz, 2H), 1.66 (m, 2H), 0.97 (t, J = 7.4 Hz, 3H). Some of the 13C signal show up twice, the signal with lower intensity is marked with an asterisk (). 13C NMR (101 MHz, d6-DMSO) delta 171.7 (C), 161.1 (C), 159.2 (C), 156.1 (C), 155.8 (C), 150.6 (C), 150.0 (C), 148.8 (C), 148.8 (C), 146.2 (C), 144.6 (CH), 136.9 (C), 137.02 (C), 129.6 (CH), 121.5 (CH), 114.9 (CH), 111.6 (CH), 42.7 (CH2), 42.1 (CH2), 35.3 (CH2), 34.4 (CH2), 34.0 (CH2), 17.9 (CH2*), 17.8 (CH2), 13.3 (CH3). LCMS: m/z (ESI 20 V) 408.1 (MH+, 100). HRMS (C20H21N7O3): calc?d 408.1779 [M+H]+, found 408.1791. HPLC: tR 9.59 min, ?99% (214 nm), ?99% (254 nm).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3427 - 3433

13
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Yield	Reaction Conditions	Operation in experiment
74%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 7.5h;	4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl) phenol (5) (50.0 mg, 148 mumol) was suspended in dichloromethane (2 mL) and trifluoroacetic acid (2 mL) was added. Decanoyl chloride (33.8 mul, 163 mumol) was drop wise added at room temperature. After 1 h and 2.5 h another equivalent of decanoyl chloride (33.8 muL, 163 mumol) was drop wise added to the reaction mixture. After 4 h reaction time the solvent was removed under vacuum. The crude material was purified by column chromatography (dichloromethane 100% ? dichloromethane: methanol 95:5). Extraction with NaHCO3, Na2CO3 water and brine was necessary to remove remaining decanoic acid. Organic layer was dried with sodium sulfate, filtered and dried on high vacuum. The title compound 48 was obtained as a white solid (53.6 mg, 74%), mp: 176-179 C. 1H NMR (400 MHz, d6-DMSO) delta 8.55 - 8.00 (2 br s, ratio 1:5, 2H), 7.87 (s, 1H), 7.53 (2 br t, J = 5.4 Hz, ratio 1:2, 1H), 7.29 (m, 2H), 7.11 - 6.98 (m, 3H), 6.68 (m, 1H), 3.52 (m, 2H), 2.89 (m, 2H), 2.54 (t, J = 7.4 Hz, 2H), 1.70 - 1.55 (m, 2H), 1.38 - 1.20 (m, 12H), 0.85 (t, J = 6.8 Hz, 3H). Some of the 13C signal show up twice, the signal with lower intensity is marked with an asterisk (). 13C NMR (101 MHz, d6-DMSO) delta 171.8 (C), 161.5 (C), 161.1 (C), 159.2 (C), 156.4 (C), 155.8 (C), 150.7 (C), 150.0 (C), 148.8 (C), 148.8 (C), 146.2 (C), 144.5 (CH), 137.0 (C), 129.5 (CH), 121.5 (CH), 111.8 (CH), 111.6 (CH), 42.7 (CH2), 42.1 (CH2), 34.4 (CH2), 34.0 (CH2), 33.4 (CH2), 31.3 (CH2), 31.2 (CH2), 28.8 (CH2), 28.8 (CH2), 28.7 (CH2), 28.7 (CH2), 28.6 (CH2), 28.4 (CH2), 28.4 (CH2), 24.3 (CH2), 22.1 (CH2), 22.1 (CH2), 13.9 (CH2*), 13.9 (CH3). LCMS: m/z (ESI 20 V) 492.2 (MH+, 100). HRMS (C26H33N7O3): calc?d 492.2718 [M+H]+, found 492.2717. HPLC: tR 12.52 min, ?99% (214 nm), ?99% (254 nm).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3427 - 3433

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[ 139180-30-6 ]

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[ 6601-22-5 ]
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N₅-(4-((4-chloro-6-morpholino-1,3,5-triazin-2-yl)oxy)phenethyl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine [ No CAS ]