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[ CAS No. 1431411-18-5 ] {[proInfo.proName]}

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Product Details of [ 1431411-18-5 ]

CAS No. :1431411-18-5 MDL No. :MFCD28098923
Formula : C7H4ClN3OS Boiling Point : -
Linear Structure Formula :- InChI Key :UGHXFHLQVJRWID-UHFFFAOYSA-N
M.W : 213.64 Pubchem ID :71654770
Synonyms :

Calculated chemistry of [ 1431411-18-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.52
TPSA : 97.11 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 1.48
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 0.45
Log Po/w (SILICOS-IT) : 2.41
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.611 mg/ml ; 0.00286 mol/l
Class : Soluble
Log S (Ali) : -3.13
Solubility : 0.16 mg/ml ; 0.000748 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.81
Solubility : 0.331 mg/ml ; 0.00155 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.34

Safety of [ 1431411-18-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1431411-18-5 ]

* 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.

  • Downstream synthetic route of [ 1431411-18-5 ]

[ 1431411-18-5 ] Synthesis Path-Downstream   1~42

  • 2
  • [ 103-76-4 ]
  • [ 1431411-18-5 ]
  • [ 1431412-13-3 ]
YieldReaction ConditionsOperation in experiment
77% With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 18h;
77% With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 18h; 28.1 Step 1. Synthesis of 4-(4-(2-hydroxyethyl)piperazin- 1-yl)thieno [3,2-dj pyrimidine-6-carboxamide (Compound 44): A solution of 4-chlorothieno [3 ,2-d]pyrimidine-6-carboxamide (14; 0.100 g, 0.468 mmol) and 2-(piperazin-1-yl)ethanol (0.073 g, 0.56 mmol) and DIEA (122 tL, 0.7 mmol) in CH3CN was heated at 60 °C for 18 h. The reaction mixture was concentrated to dryness, resuspended in dilute aq. NaHCO3 and collected by filtration. The filter cake was dried under vacuum to obtain 4-(4-(2-hydroxyethyl)piperazin- 1 -yl)thieno[3 ,2-d]pyrimidine-6- carboxamide (Compound 44; 0.111 g, 77%). MS (ESI)calcdforCi3Hi7N5O2S: 307.37; found: 308 [M+H].
  • 3
  • [ 16269-66-2 ]
  • [ 1431411-18-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3.5 h / 0 °C / Inert atmosphere; Reflux 3.1: ammonia / 1,4-dioxane / 0.67 h / 0 °C
Multi-step reaction with 2 steps 1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: 2 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3.67 h / 0 - 60 °C 2.2: 0.67 h / 0 °C
  • 5
  • [ 1431411-18-5 ]
  • [ 165528-81-4 ]
  • [ 1431411-20-9 ]
YieldReaction ConditionsOperation in experiment
90% With N-ethyl-N,N-diisopropylamine In acetonitrile at 85℃; for 1h;
90% With N-ethyl-N,N-diisopropylamine In acetonitrile for 1h; Reflux; 10 Example 10. Preparation of tert-butyl (2-(1-(6-carbamoylthieno[3,2-djpyrimidin-4- yl)piperidin-4-yl)ethyl)carbamate (Compound 1 5a): A solution of 4-chlorothieno[3,2-d]pyrimidine-6-carboxamide (14; 1.30 g, 6.08 mmol), tert-butyl(2-(piperidin-4-yl)ethyl)carbamate (1.39 g, 6.08 mmol) and DIEA (1.05 mL, 6.08mmol) in CH3CN (80 mL) was heated at reflux for 1 hour. The reaction mixture was cooled to room temperature and concentrated to dryness. The residue was suspended in MeOH (10 mL) then water (90 mL) was added. The mixture was sonicated and the precipitate was collected by filtration, washed with water and dried under high vacuum to obtain tert-butyl (2-( 1 -(6-carbamoylthieno [3 ,2-d]pyrimidin-4-yl)piperidin-4-yl)ethyl)carbamate (Compound iSa; 2.23 g, 90%). MS (ESI) calcd for C19H27N5035:405.18; found: 406 [M+H].
  • 6
  • [ 140447-78-5 ]
  • [ 1431411-18-5 ]
  • [ 1431411-22-1 ]
YieldReaction ConditionsOperation in experiment
93% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 60℃; for 18h; A solution of 4-chlorothieno[3,2-d]pyrimidine-6-carboxamide (14; 0.250 g, 1.17 mmol),DIEA (245 jiL, 1.40 mmol) and <strong>[140447-78-5]tert-butyl (2-(piperazin-1-yl)ethyl)carbamate</strong> (0.332 g,1.40 mmol) in CH3CN (15 mL) was heated at 60C for 18 hours. The reaction mixturewas cooled to room temperature and filtered to collect the product as a solid. The solid was washed with CH3CN (2 x 10 mL) and dried to obtain tert-butyl (2-(4-(6- carbamoylthieno [3 ,2-d]pyrimidin-4-yl)piperazin- 1 -yl)ethyl)carbamate as a white solid (Compound 15b; 0.440 g, 93%). MS (ESI) calcd for C18H26N6035: 406.18; found: 407 [M+H].
  • 9
  • [ 875515-76-7 ]
  • [ 1431411-18-5 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: 4-chlorothieno[3,2-d]pyrimidine-6-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 60℃; for 3.66667h; Stage #2: With ammonia In 1,4-dioxane at 0℃; for 0.666667h; 7.2 Step 2. Synthesis of 4-chiorothieno [3,2-dj pyrimidine-6-carboxamide (Compound 14): To a solution of oxalyl chloride (4.17 mL, 47 mmol) in anhydrous dichloromethane (50 mL) at 0 °C under nitrogen was added DMF (0.8 mL). The solution was stirred at 0 °C for30 minutes, and then a suspension of 4-chlorothieno[3,2-d]pyrimidine-6-carboxylic acid (13; 5.04 g, 23.5 mmol) in dichloromethane (50 mL) was added dropwise over 10 minutes at 0 °C. The reaction mixture was heated to 60 °C for 3.5 hours and concentrated to dryness. The crude acid chloride was dissolved in dioxane (80 mL) and 182 mL (91 mmol) of a solution of 0.5 M ammonia in dioxane was added dropwise over 10 mm at 0°C. The reaction mixture was stirred at 0 °C for 30 mi warmed to room temperature, diluted with water (150 mL) and extracted with CH2C12 (3x). The combined organic layers were washed with water (2x), dilute aq. NaHCO3, brine and concentrated to dryness. The product was recrystallized from CH3CN to obtain 4-chlorothieno[3,2-d]pyrimidine-6- carboxamide (Compound 14; 0.842 g). The mother liquor was concentrated to obtain asecond crop (Compound 14; 1.499 g) and a third crop (Compound 14; 0.259 g) of 4- chlorothieno[3,2-d]pyrimidine-6-carboxamidefor a total of 2.6 g (52%) of Compound 14. MS (ESI) calcd for C7H4C1N3OS: 212.98; found: 214.0 [M+H].
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3.5 h / 0 °C / Inert atmosphere; Reflux 2: ammonia / 1,4-dioxane / 0.67 h / 0 °C
  • 10
  • [ 1431411-18-5 ]
  • C13H16ClN5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 6 h / 20 °C
  • 11
  • [ 1431411-18-5 ]
  • [ 1431411-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 85 °C 2: trifluoroacetic acid / dichloromethane / 72 h 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h
  • 12
  • [ 1431411-18-5 ]
  • [ 1431411-30-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: dichloromethane / 6 h 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h
  • 13
  • [ 1431411-18-5 ]
  • [ 1431411-32-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 85 °C 2: trifluoroacetic acid / dichloromethane / 72 h 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h
  • 14
  • [ 1431411-18-5 ]
  • [ 1431411-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: dichloromethane / 6 h 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h
  • 15
  • [ 1431411-18-5 ]
  • [ 1431411-43-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 80 °C 2.1: dichloromethane / 4 h / 20 °C 3.1: sodium carbonate / water; ethyl acetate / 0.08 h / 20 °C 3.2: 20 °C
  • 16
  • [ 1431411-18-5 ]
  • [ 1431411-52-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: dichloromethane / 6 h 3: sodium carbonate / water; ethyl acetate / 20 °C
  • 17
  • [ 1431411-18-5 ]
  • [ 1431411-56-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: dichloromethane / 6 h 3: sodium carbonate / water; ethanol / 20 °C
  • 19
  • [ 1431411-18-5 ]
  • [ 1431411-58-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetonitrile / 18 h / 80 °C 2: hydrogenchloride / tetrahydrofuran; water / 3 h / 20 °C 3: sodium carbonate / water; ethyl acetate / 20 °C
  • 20
  • [ 1431411-18-5 ]
  • [ 1431412-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 80 °C 2: dichloromethane / 4 h / 20 °C
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 80 °C 2: dichloromethane / 4 h / 20 °C
  • 21
  • [ 1431411-18-5 ]
  • [ 1431411-62-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 80 °C 2.1: dichloromethane / 4 h / 20 °C 3.1: sodium carbonate / water; ethyl acetate / 0.08 h / 20 °C 3.2: 18 h / 20 °C
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 80 °C 2.1: dichloromethane / 4 h / 20 °C 3.1: sodium carbonate / water; ethyl acetate / 0.08 h / 20 °C 3.2: 18 h / 20 °C
  • 22
  • [ 1431411-18-5 ]
  • [ 1431411-64-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: dichloromethane / 6 h 3: sodium carbonate / water; ethyl acetate / 20 °C
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: dichloromethane / 6 h 3: sodium carbonate / water; ethyl acetate / 20 °C
  • 23
  • [ 1431411-18-5 ]
  • C17H24N6OS*2C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 6 h / 20 °C 3: dichloromethane / 96 h / 20 °C
  • 24
  • [ 1431411-18-5 ]
  • 4-(4-(2-aminoethyl)piperidin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 85 °C 2: trifluoroacetic acid / dichloromethane / 72 h
  • 25
  • [ 1431411-18-5 ]
  • 4-(4-(2-aminoethyl)piperazin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide bis(trifluoroacetate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: dichloromethane / 6 h
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2: dichloromethane / 6 h
  • 26
  • [ 1431411-18-5 ]
  • [ 75-04-7 ]
  • [ 1431411-47-0 ]
YieldReaction ConditionsOperation in experiment
93% In water; acetonitrile at 60℃; for 18h;
93% In water; acetonitrile at 60℃; for 18h; 42 Example 42. Preparation of 4-(Ethylamino)thieno[3,2-djpyrimidine-6-carboxamide. (Compound 22): A solution of 4-chlorothieno [3 ,2-d]pyrimidine-6-carboxamide (14, 0.085 g, 0.500 mmol) and 70% ethylamine in water (200 tL, excess) in CH3CN (5 mL) was heated at 60 °C for18 hours. The reaction mixture was concentrated to dryness and purified by prep-HPLC to obtain 4-(ethylamino)thieno [3 ,2-d]pyrimidine-6-carboxamide (Compound 22; 0.083 g, 93%). MS (ESI) calcd for C9H10N405: 222.06; found: 223 [M+H].
  • 27
  • [ 1431411-18-5 ]
  • [ 1247739-31-6 ]
  • [ 1431411-60-7 ]
YieldReaction ConditionsOperation in experiment
75% With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃;
75% With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; 23.3 Step 3. Synthesis of 4-(4-(2-pivalamidoethyl)piperidin- 1-yl)thieno [3,2-dj pyrimidine-6- carboxamide (Compound 28): A solution of 4-chlorothieno[3,2-d]pyrimidine-6-carboxamide (14; 0.534 g, 2.5 mmol) andN-(2-(piperidin-4-yl)ethyl)pivalamide (0.530 g, 2.5 mmol) and DIEA (866 iL, 5 mmol) inCH3CN (30 mL) was heated at 80 °C overnight. The reaction mixture was concentratedand purified on silica gel chromatography (0 to 10% MeOH gradient in CH2C12) to obtain4-(4-(2-pivalamidoethyl)piperidin- 1 -yl)thieno [3 ,2-d]pyrimidine-6-carboxamide (Compound 28; 0.727 g, 75%) as a yellow solid MS (ESI) calcd for C19H27N5025: 389.19; found: 390 [M+H].
  • 28
  • [ 1431411-18-5 ]
  • N-(2-(piperazin-1-yl)ethyl)methanesulfonamide bis-2,2,2-trifluoroacetate [ No CAS ]
  • C14H20N6O3S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 18h;
  • 29
  • [ 110-89-4 ]
  • [ 1431411-18-5 ]
  • [ 1431411-45-8 ]
YieldReaction ConditionsOperation in experiment
82% In acetonitrile at 60℃; for 18h;
82% In acetonitrile at 60℃; for 18h; 41 Example 41. Prepration of 4-(Piperidin-1-yl)thieno [3,2-dj pyrimidine-6-carboxamide. (Compound 21): A solution of 4-chlorothieno [3 ,2-d]pyrimidine-6-carboxamide (14, 0.085 g, 0.500 mmol)and piperidine (0.34 g, 4 mmol) in CH3CN (5 mL) was heated at 60 °C for 18 hours. Thereaction mixture was concentrated to dryness and purified by prep-HPLC to obtain 4- (piperidin- 1 -yl)thieno [3 ,2-d]pyrimidine-6-carboxamide (Compound 21; 0.086 g, 82%). MS (ESI) calcd for C12H14N405: 262.09; found: 263 [M+H].
  • 30
  • [ 1431411-18-5 ]
  • [ 135632-53-0 ]
  • [ 1431411-96-9 ]
YieldReaction ConditionsOperation in experiment
95% In acetonitrile at 80℃; for 18h;
95% In acetonitrile at 80℃; for 18h; 15 Example 15. Preparation of tert-butyl ((1-(6-carbamoylthieno [3,2-dj pyrimidin-4- yl)piperidin-4-yl)methyl)carbamate (Compound 57): A solution of 4-chlorothieno[3,2-d]pyrimidine-6-carboxamide (14; 0.128 g, 0.6 mmol) andtert-butyl (piperidin-4-ylmethyl)carbamate (0.193 g, 0.9 mmol) in CH3CN was heated at80 °C for 18 h. The reaction mixture was concentrated to dryness, suspended in EtOAc, washed with sat. NaHCO3, water, brine, dried (Na2SO4), and concentrated to dryness. The crude product was purified by flash chromatography (0 to 10% MeOH in CH2C12 gradient) to obtain tert-butyl ((1 -(6-carbamoylthieno [3 ,2-d]pyrimidin-4-yl)piperidin-4-yl)methyl)carbamate (Compound 57; 0.224 g, 95%). MS (ESI) calcd for C18H25N5035:391.17; found: 392 [M+H].
  • 31
  • N-(2-(piperidin-4-yl)ethyl)methanesulfonamide hydrochloride [ No CAS ]
  • [ 1431411-18-5 ]
  • [ 1431411-66-3 ]
YieldReaction ConditionsOperation in experiment
67% With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 24h;
  • 32
  • 4-(3-N-tert-butoxycarbonylaminopropyl)piperidine [ No CAS ]
  • [ 1431411-18-5 ]
  • [ 1431412-03-1 ]
YieldReaction ConditionsOperation in experiment
62% With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 20h;
62% With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 20h; 24.5 Step 5. Synthesis of tert-butyl (3-(1-(6-carbamoylthieno[3,2-djpyrimidin-4- yl)piperidin-4-yl)propyl)carbamate (Compound 76): A solution of 4-chlorothieno [3 ,2-d]pyrimidine-6-carboxamide (14; 0.176 g, 0.82 mmol),tert-butyl (3-(pyridin-4-yl)propyl)carbamate (75; 0.200 g, 0.82 mmol) and DIEA (573 tL,3.3 mmol) in CH3CN (20 mL) was heated at 80 °C for 20 h. The reaction mixture was concentrated to dryness, and purified by column chromatography (0 to 10% MeOHgradient in CH2C12) to obtain tert-butyl (3 -(1 -(6-carbamoylthieno [3 ,2-d]pyrimidin-4- yl)piperidin-4-yl)propyl)carbamate (Compound 76; 0.2 16 g, 62%). MS (ESI) calcd for C20H29N5035: 419.20; found: 420 [M+H].
  • 33
  • [ 1431411-18-5 ]
  • N,N-dimethyl-1-(piperidin-4-yl)methanamine [ No CAS ]
  • 4-(4-((dimethylamino)methyl)piperidin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 100℃; for 2h; 7.3 Step 3. Synthesis of 4-(4-((dimethylamino)methyl)piperidin-1-yl)thieno [3,2- dj pyrimidine-6-carboxamide (Compound 43): A solution of 4-chlorothieno [3 ,2-d]pyrimidine-6-carboxamide (14; 0.043 g, 0.200 mmol), N,N-dimethyl-1-(piperidin-4-yl)methanamine (0.028 g, 0.200 mmol) and DIEA (42 jiL, 0.24 mmol) in NMP (1 mL) was heated to 100 °C for 2 hours. The reaction mixture was concentrated to dryness, and the residue was dissolved in DMSO and purified by mass directed prep-HPLC. The fractions were lyophilized to obtain 4-(4- ((dimethylamino)methyl)piperidin- 1 -yl)thieno [3 ,2-d]pyrimidine-6-carboxamide as the TFA salt (Compound 43; 0.039 g, 46%).MS (ESI) calcd for C15H21N505: 319.15; found:320 [M+H].
  • 34
  • N-(piperidin-4-ylmethyl)acetamide [ No CAS ]
  • [ 1431411-18-5 ]
  • 4-(4-(acetamidomethyl)piperidin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 80℃; for 1.5h; 8 Example 8. Preparation of 4-(4-(acetamidomethyl)piperidin-1-yl)thieno [3,2- dj pyrimidine-6-carboxamide (Compound 23): A solution of 4-chlorothieno [3 ,2-d]pyrimidine-6-carboxamide (0.043 g, 0.200 mmol) and N-(piperidin-4-ylmethyl)acetamide (14; 0.031 g, 0.200 mmol) in pyridine (1 mL) was heated at 80 °C for 1.5 hours. The reaction mixture was concentrated to dryness, and purified by mass directed prep-HPLC to obtain 4-(4-(acetamidomethyl)piperidin- 1-yl)thieno[3,2-d]pyrimidine-6-carboxamide as the TFA salt (Compound 23; 0.052 g, 37%). MS (ESI) calcd for C15H19N5025: 333.13; found: 334 [M+H].
  • 35
  • [ 1431411-18-5 ]
  • 4-(5,5-dimethyl-1,3-dioxan-2-yl)piperidine oxylate [ No CAS ]
  • 4-(4-(5,5-dimethyl-1,3-dioxan-2-yl)piperidin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; 26 Example 26. Preparation of 4-(4-(5,5-dimethyl- 1 ,3-dioxan-2-yl)piperidin- 1- yl)thieno [3,2-dj pyrimidine-6-carboxamide (Compound 78): A solution of 4-chiorothieno [3 ,2-d]pyrimidine-6-carboxamide (14; 0.712 g, 3.33 mmol) and 4-(5 ,5-dimethyl- 1 ,3-dioxan-2-yl)piperidine oxylate (1.06 g, 3.66 mmol) and DIEA (1.73 mL, 10 mmol) in CH3CN (30 mL) was heated at 80 °C overnight. The reactionmixture was concentrated to dryness. Aqueous NaHCO3 (sat) was added, and the solution was extracted with ethyl acetate (2x), and filtered to recover the rag layer (0.516 g of crude product which was reserved). The organic layer was washed with water, brine, dried (Na2SO4) and concentrated to obtain 0.7 15 g of crude product. The crude products were combined and purified by column chromatography (0 to 10% MeOH in CH2C12 gradient)to obtain 4-(4-(5 ,5-dimethyl- 1 ,3-dioxan-2-yl)piperidin- 1 -yl)thieno[3 ,2-d]pyrimidine-6- carboxamide (Compound 78; 0.926 g, 74%). MS (ESI) calcd for C18H24N4035: 376.16; found: 377 [M+H].
  • 36
  • [ 1431411-18-5 ]
  • N-(2-(piperazin-1-yl)ethyl)methanesulfonamide bis-2,2,2-trifluoroacetate [ No CAS ]
  • 4-(4-(2-(methylsulfonamido)ethyl)piperazin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 18h; 27.3 Step 3. Synthesis of 4-(4-(2-(Methylsulfonamido)ethyl)piperazin-1-yl)thieno [3,2- dj pyrimidine-6-carboxamide 2,2,2-trifluoroacetate (Compound 32): A solution of 4-chiorothieno [3 ,2-d]pyrimidine-6-carboxamide (14; 0.4 mmol, 0.085 g), N(2-(piperazin- 1 -yl)ethyl)methanesulfonamide bis(2,2,2-trifluoroacetate) (80; 0.48 mmol,0.146 g) and DIEA (208 tL, 1.2 mmol) in CH3CN and was heated to 60°C for 18 hrs. Thereaction mixture was concentrated to dryness, triturated with methanol and the solid wascollected by filtration. The product was purified by Prep-HPLC and lyophilized to afford4-(4-(2-(methylsulfonamido)ethyl)piperazin- 1 -yl)thieno [3 ,2-d]pyrimidine-6-carboxamide(Compound 32; 0.030 g, 15%). MS (ESI) calcd for C14H20N60352: 384.10; found: 385[M+H].
  • 37
  • [ 1431411-18-5 ]
  • 4-(4-(2-aminoethyl)piperidin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / Reflux 2: dichloromethane / 3 h
  • 38
  • [ 1431411-18-5 ]
  • 4-(4-(aminomethyl)piperidin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 18 h / 80 °C 2: hydrogenchloride / tetrahydrofuran; water / 3 h / 20 °C
  • 39
  • [ 1431411-18-5 ]
  • [ 1431411-54-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / Reflux 2: dichloromethane / 3 h 3: sodium carbonate / water; ethanol / 6 h / 20 °C
  • 40
  • [ 1431411-18-5 ]
  • 4-(4-(2-(pyrrolidin-1-yl)ethyl)piperazin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 60 °C 2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 6 h / 20 °C 2.2: 96 h / 20 °C
  • 41
  • [ 1431411-18-5 ]
  • 5-bromo-N1-(2-(1-(6-carbamoylthieno[3,2-d]pyrimidin-4-yl)piperidin-4-yl)ethyl)-N3-ethylisophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / Reflux 2: dichloromethane / 3 h 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C
  • 42
  • [ 1431411-18-5 ]
  • 1-(piperidin-4-ylmethyl)-3-(trifluoromethyl)piperidine [ No CAS ]
  • 4-(4-((3-(trifluoromethyl)piperidin-1-yl)methyl)piperidin-1-yl)thieno[3,2-d]pyrimidine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In acetonitrile at 85℃; for 72h; 36.3 Step 3. Synthesis of 4-(4-((3-(trifluoromethyl)piperidin- 1-yl)methyl)piperidin-1- yl)thieno [3,2-dj pyrimidine-6-carboxamide (Compound 131): 1 -(Piperidin-4-ylmethyl)-3 -(trifluoromethyl)piperidine (130; assumed 0.5 mmol), 4-chiorothieno [3 ,2-d]pyrimidine-6-carboxamide (14; 0.071 g, 0.333 mmol) and DIEA (230tL, 1.33 mmol) in CH3CN (5 mL) was heated at 85°C for 3 days and concentrated todryness. The residue was purified by prep-HPLC to obtain 4-(4-((3-(trifluoromethyl)piperidin- 1 -yl)methyl)piperidin- 1 -yl)thieno [3 ,2-d]pyrimidine-6-carboxamide as the bis-TFA salt (Compound 131; 0.05 1 g, 8%). MS (ESI) calcd forC19H24F3N505: 427.17; found: 428 [M+H].
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