Home Cart 0 Sign in  

[ CAS No. 871657-49-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 871657-49-7
Chemical Structure| 871657-49-7
Structure of 871657-49-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 871657-49-7 ]

Related Doc. of [ 871657-49-7 ]

Alternatived Products of [ 871657-49-7 ]

Product Details of [ 871657-49-7 ]

CAS No. :871657-49-7 MDL No. :MFCD06804558
Formula : C6H14ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :QSKVFUMEPLXIRZ-UHFFFAOYSA-N
M.W : 151.63 Pubchem ID :53249190
Synonyms :

Calculated chemistry of [ 871657-49-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.61
TPSA : 21.26 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) : -6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.09
Log Po/w (WLOGP) : 0.8
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 0.93
Consensus Log Po/w : 0.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.33
Solubility : 7.01 mg/ml ; 0.0463 mol/l
Class : Very soluble
Log S (Ali) : -1.13
Solubility : 11.3 mg/ml ; 0.0743 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.04
Solubility : 13.9 mg/ml ; 0.0914 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 871657-49-7 ]

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

Application In Synthesis of [ 871657-49-7 ]

* 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.

  • Downstream synthetic route of [ 871657-49-7 ]

[ 871657-49-7 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 871657-49-7 ]
  • [ 1599524-73-8 ]
  • 6-bromo-4-chloro-3-(4-chlorophenoxy)-2-(3-isopropoxyazetidin-1-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 60℃; Inter mediate 7: step d 6-Bromo-4-chIoro-3-(4-chIorophenoxy)-2-(3-isopropoxyazetidiii-l-yl)quiiioIiiie To 6-bromo-2,4-dichioro-3-(4-chlorophenoxy)quinoline (0.50 g, 1.24 mmol, Intermediate 7: step c) was added Lambda -dimemylformamide (3 mL) and 3-isopropoxyazetidine-HCl (0.188 g, 1.24 nimol), and the reaction was heated at 60 C overnight. The reaction was cooled, diluted with ethyl acetate and the organic layer was washed with water five times to remove the N,N- diinethyiformaniide. The organic layer was dried (MgS04), filtered and concentrated, then purified over a silica gel column with ethyl acetate/heptane to afford the title compound.
In N,N-dimethyl-formamide; at 60℃; [0216] To 6-bromo-2,4-dichloro-3-(4-chlorophenoxy) quinoline (0.50 g, 1.24 mmol, Intermediate 7: step c) was added N,N-dimethylformamide (3 mE) and 3-isopro- poxyazetidine-HC1 (0.188 g, 1.24 mmol), and the reaction was heated at 600 C. overnight. The reaction was cooled, diluted with ethyl acetate and the organic layer was washed with water five times to remove the N,N-dimethylformamide. The organic layer was dried (Mg504), filtered and concentrated, then purified over a silica gel colunm with ethyl acetate/heptane to afford the title compound.
In N,N-dimethyl-formamide; at 6℃; 6-Bromo-2,4-dichloro-3- (4-chlorophenoxy) quinoline (0.50 g, 1.24 mmol,Intermediate 7: N, N-Dimethylformamide (3 mL) was added to step c)And 3-isopropoxy azetidine-HCl (0.188 g, 1.24 mmol) were added and the reaction was heated to 6 & lt; 0 & gt; C overnight. The reaction mixture was cooled, diluted with ethyl acetate, and the organic layer was washed with water five times to remove N, N-dimethylformamide. The organic layer was dried (MgSO4), filtered and concentrated, then purified on silica gel column with ethyl acetate / heptane to give the title compound.
  • 3
  • [ 871657-49-7 ]
  • (4-(2-chloropyrimidin-4-yl)-2-methylphenyl)methanamine hydrochloride [ No CAS ]
  • [ 530-62-1 ]
  • N-(4-(2-chloropyrimidin-4-yl)-2-methylbenzyl)-3-isopropoxyazetidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% [0189j To solution of N,N-carbonyldiimidazole (1.20 g, 7.40 mmol) in THF (100 mL)was added a solution of (4-(2-chloropyrimidin-4-yl)-2-methylphenyl)methanamine hydrochloride (2.0 g, 7.40 mmol) and Et3N (1.0 mL, 7.40 mmol). The mixture was stirred at rt for 12 h, followed by the addition of <strong>[871657-49-7]3-isopropoxyazetidine hydrochloride</strong> (1.12 g, 7.40 mmol) and Et3N (2.1 mL, 14.8 mmol), and then stirred at rt for 12 h. The solvent was removed in vacuo to afford the crude which was purified by silica gel chromatography (EtOAc/heptane gradient) to give N-(4-(2-chloropyrimidin-4-yl)-2-methylbenzyl)-3 -isopropoxyazetidine- 1 -carboxamide as a white powder (1.68 g, yield: 60%). LCMS: RT 1.40 mm.; MH+ 375.1; ?H NMR (400 MHz, DMSO-d6) (5: 9.06 (d, J = 0.75 Hz, 1H), 8.28 (s, 1H), 7.99 - 8.13 (m, 2H), 7.36 (d, J = 8.53 Hz,1H), 6.87 (t, J = 5.77 Hz, 1H), 4.16 - 4.41 (m, 3H), 4.04 (dd, J = 6.78, 8.53 Hz, 2H), 3.51 - 3.69 (m, 3H), 2.36 (s, 3H), 1.08 (d, J = 6.27 Hz, 6H).
  • 4
  • [ 871657-49-7 ]
  • 4-(4-(aminomethyl)-3-methylphenyl)-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine hydrochloride [ No CAS ]
  • [ 530-62-1 ]
  • 3-((propan-2-yl)oxy)-N-(2-methyl-4-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)benzyl)azetidine-1-carboxamide trifluoroaceti acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% [0186j To a solution of N,N-carbonyldiimidazole (66.1 mg, 0.4077 mmol) in tetrahydrofuran (5 mL, 60 mmol) was added 4-(4-(aminomethyl)-3-methylphenyl)-N-(i-methyl- 1H-pyrazol-4-yl)pyrimidin-2-amine (120.0 mg, 0.4077 mmol) and triethylamine (0.17 mL, 1.223 mmol) . The mixture was stirred at RT for 2h. 3-((2-d-propan-2-yl)oxy)azetidine hydrochloride (124.4 mg, 0.8 153 mmol) was then added. The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc, washed with water. The organic phase was separated, dried and concentrated. The crude was purified by HPLC to give 3-((2-D-propan-2-yl)oxy)-N-(2- methyl-4-(2-(( i-methyl-i H-pyrazol-4-yl)amino)pyrimidin-4-yl)benzyl)azetidine- 1 -carboxamide as a yellow powder (155 mg, TFA salt, yield: 87%). LCMS: RT 1.06 mm.; MH+ 437.2; ?H NMR (400 MHz, DMSO-d6) d 9.53 (s, 1H), 8.45 (d, J = 5.27 Hz, 1H), 7.93 (s, 3H), 7.56 (br. s., 1H), 7.36 (d, J = 8.28 Hz, 1H), 7.26 (d, J = 5.27 Hz, 1H), 6.85 (t, J = 5.27 Hz, 1H), 4.27 - 4.38 (m, 1H), 4.23 (d, J = 4.77 Hz, 2H), 3.98 - 4.09 (m, 2H), 3.83 (s, 3H), 3.62 (dd, J = 4.64, 8.66 Hz, 2H), 2.37 (s, 3H), 1.07 (s, 6H).
  • 5
  • [ 871657-49-7 ]
  • 2-bromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-amine [ No CAS ]
  • [ 530-62-1 ]
  • N-(2-bromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)-3-isopropoxyazetidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% [0475j To a mixture of 2-bromo-6,7, 8 ,9-tetrahydro-5H-benzo [7]annulen-5 -amine (200 mg, 0.84 mmol) in DMF (5 mL), CDI (118 mg, 0.84 mmol) and TEA (340 mg, 3.40 mmol) was added. The mixture was stirred at room temperature for 1 h followed by addition of 3- isopropoxyazetidine hydrochloride (127 mg, 0.84 mmol). The resulting mixture was stirred at rt for another 12 h. After diluting with CH2C12 (150 mL), the mixture was washed with brine (50 mL x 2). The organic phase was concentrated in vacuo and the residue was purified by prepHPLC (Gradient: 5% B increase to 95% B, A: 0.5% NH3 in water, B: CH3CN) to give N-(2- bromo-6,7, 8 ,9-tetrahydro-5H-benzo [7] annulen-5 -yl)-3 -isopropoxyazetidine- 1 -carboxamide (290 mg, yield: 74%) as a white solid. ESI-MS (M+1): 381.1. ?H NMR (400 MHz, CDC13) 8:7.27- 7.23 (m, 2H), 7.08 (d,J= 8.0 Hz, 1H), 4.98-4.97 (m, 1H), 4.41-4.32 (m, 2H), 4.16-4.11(m, 2H),3.89-3.84 (m, 2H), 3.64-3.58 (m, 1H), 2.87-2.70 (m, 2H), 1.89-1.74 (m, 5H), 1.54-1.49 (m, 1H),1.16 (d, J= 5.6 Hz, 6H).
  • 6
  • [ 871657-49-7 ]
  • tert-butyl 5-amino-8-bromo-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carboxylate [ No CAS ]
  • [ 530-62-1 ]
  • tert-butyl-8-bromo-5-(3-isopropoxyazetidine-1-carboxamido)-4,5-dihydro-1H-benzo[c]azepine-2-(3H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% [0520j To a solution of tert-butyl 5 -amino-8-bromo-4,5 -dihydro- 1H-benzo [c]azepine2(3H)-carboxylate (300 mg, 0.90 mmol) in DMF (4 mL) was added TEA (138 mg, 1.35 mmol) and CDI (219 mg, 1.35 mmol). After stirring at rt for 1 h, 3-isopropoxyazetidine (204 mg, 1.35 mmol) was added to the solution. The resulting solution was stirred for another 1 h. The mixture was purified by prep-HPLC (CH3CN/H20 with 0.05% NH3.H20 as mobile phase) to give tertbutyl 8-bromo-5 -(3 -isopropoxyazetidine- 1 -carboxamido)-4,5 -dihydro- 1 H-benzo [c] azepine-2- (3H)-carboxylate as white solid. (178 mg, yield: 42%). ESI-MS (M+H)482.2.
  • 7
  • [ 871657-49-7 ]
  • 4-(6-fluoropyridin-3-yl)-6-(2-hydroxy-2-methylpropoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile [ No CAS ]
  • 6-(2-hydroxy-2-methylpropoxy)-4-(6-(3-isopropoxyazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.2% With triethylamine; In N,N-dimethyl acetamide; at 90℃; A mixture of 4-(6-fluoropyridin-3-yl)-6-(2-hydroxy-2- methylpropoxy)pyrazolo[l,5-a]pyridine-3-carbonitrile (Intermediate P42; 35 mg, 0.107 mmol), 3-(l-methylethoxy)-azetidine hydrochloride (48.8 mg, 0.322 mmol) and TEA (73 mu^, 0.536 mmol) in DMA (358 mu.) was stirred overnight at 90C. After cooling to ambient temperature, the reaction mixture was diluted with DCM and washed with water. The organic extracts were washed with brine and dried over anhydrous Na2S04(s), filtered and concentrated in vacuo. The residue was suspended in 60:40 ACN:water containing 2% TFA. The solution was purified directly by C18 reverse phase chromatography (5-95% ACN in water with 0.1% TFA as the gradient eluent) to afford the title compound as the TFA salt. The TFA salt was treated with saturated NaHCCbtaq) and extracted with DCM. The combined organic extracts were washed with brine, then dried over anhydrous Na2S04(S), filtered and concentrated in vacuo to afford the title compound (16.8 mg, 37.2% yield). MS (apci) m/z = 422.20 (M+H).
  • 8
  • [ 871657-49-7 ]
  • 6-[(pyrazin-2-yl)({5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophen-2-yl}methyl)amino]pyridazine-4-carboxylic acid [ No CAS ]
  • 5-[3-(propan-2-yloxy)azetidine-1-carbonyl]-N-(pyrazin-2-yl)-N-({5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophen-2-yl}methyl)pyridazin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% (1451) To a solution of acid 1 (50 mg, 0.1 1 mmol) in DMF (1 ml_) was added N- methylmorpholine (49 mI_, 0.45 mmol) followed by PyBOP (87 mg, 0.17 mmol). The reaction mixture was stirred for 50 min at rt before addition of 3- (isopropoxy)azetidine hydrochloride (34 mg, 0.22 mmol). After 26 h the reaction mixture was diluted with EtOAc (30 ml_), washed with HCI solution (5%, 3 x 10 ml_), water (10 ml_), sodium bicarbonate solution (5%, 3 x 5 ml_), and brine (10 ml_), before being dried over MgS04, filtered and concentrated in vacuo. Purification by flash column chromatography with hexanes/EtOAc (1 :0 to 0:1 ) afforded GC as pale yellow solids (38 mg, 62%). (1452) LCMS (ES): Found 546.9 [M+Hf. (1453) 1H NMR (300 MHz, DMSO-cf6) d: 9.03 (d, J=1.7 Hz, 1 H), 8.83 (d, J=1.3 Hz, 1 H), 8.40 (dd, J=2.6, 1.5 Hz, 1 H), 8.32 (d, J=2.6 Hz, 1 H), 7.84 (d, J=1.7 Hz, 1 H), 7.74 (d, J=3.8 Hz, 1 H), 7.31 (d, J=3.8 Hz, 1 H), 5.76 (d, J=1.9 Hz, 2H), 4.35-4.51 (m, (1454) 2H), 4.25-4.35 (m, 1 H), 4.14-4.22 (m, 1 H), 3.77-3.87 (m, 1 H), 3.61 (spt, J=6.2 Hz, 1 H), 1.08 (t, J=5.7 Hz, 6H). (1455) 19F NMR (282 MHZ, DMSO-cf6) d: -64.80 (s, 3F).
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 871657-49-7 ]

Ethers

Chemical Structure| 148644-09-1

[ 148644-09-1 ]

3-Methoxyazetidine hydrochloride

Similarity: 0.96

Chemical Structure| 907545-98-6

[ 907545-98-6 ]

(R)-2-Methoxypropan-1-amine hydrochloride

Similarity: 0.78

Chemical Structure| 907544-43-8

[ 907544-43-8 ]

(S)-2-Methoxypropan-1-amine hydrochloride

Similarity: 0.78

Chemical Structure| 70807-90-8

[ 70807-90-8 ]

2-Methoxypropan-1-amine hydrochloride

Similarity: 0.78

Chemical Structure| 144053-99-6

[ 144053-99-6 ]

2-(Methoxymethyl)morpholine hydrochloride

Similarity: 0.73

Related Parent Nucleus of
[ 871657-49-7 ]

Aliphatic Heterocycles

Chemical Structure| 148644-09-1

[ 148644-09-1 ]

3-Methoxyazetidine hydrochloride

Similarity: 0.96

Chemical Structure| 59229-57-1

[ 59229-57-1 ]

2-Methylmorpholine hydrochloride

Similarity: 0.85

Chemical Structure| 168038-14-0

[ 168038-14-0 ]

(R)-2-Methylmorpholine hydrochloride

Similarity: 0.85

Chemical Structure| 1147108-99-3

[ 1147108-99-3 ]

(S)-2-Methylmorpholine hydrochloride

Similarity: 0.85

Chemical Structure| 276252-73-4

[ 276252-73-4 ]

(2S,6S)-2,6-Dimethylmorpholine

Similarity: 0.81

Azetidines

Chemical Structure| 148644-09-1

[ 148644-09-1 ]

3-Methoxyazetidine hydrochloride

Similarity: 0.96

Chemical Structure| 18621-18-6

[ 18621-18-6 ]

Azetidin-3-ol hydrochloride

Similarity: 0.78

Chemical Structure| 74121-99-6

[ 74121-99-6 ]

Azetidin-3-yl acetate

Similarity: 0.73

Chemical Structure| 124668-46-8

[ 124668-46-8 ]

3-Methylazetidin-3-ol hydrochloride

Similarity: 0.67

Chemical Structure| 897019-59-9

[ 897019-59-9 ]

3-(Benzyloxy)azetidine hydrochloride

Similarity: 0.58