7-bromo-N-(1-phenylcyclopropyl)-3-[(4-piperidin-1-ylpiperidin-1-yl) methyl]-2-[3-(trifluoromethyl)phenyl]quinoline-4-carboxamide

Base Information

• Chemical Name: 7-bromo-N-(1-phenylcyclopropyl)-3-[(4-piperidin-1-ylpiperidin-1-yl) methyl]-2-[3-(trifluoromethyl)phenyl]quinoline-4-carboxamide
• CAS No.: 1336960-13-4
• Molecular Formula: C₃₇H₃₈BrF₃N₄O
• Molecular Weight: 691.634
• European Community (EC) Number: 808-437-6
• Wikidata: Q27077882
• Pharos Ligand ID: TNH23X4DBGUG
• ChEMBL ID: CHEMBL4073922
• Mol file: 1336960-13-4.mol

Synonyms:7-bromo-N-(1-phenylcyclopropyl)-3-((4-piperidin-1-ylpiperidin-1-yl)methyl)-2-(3-(trifluoromethyl)phenyl)quinoline-4-carboxamide;GSK2193874

Chemical Property of 7-bromo-N-(1-phenylcyclopropyl)-3-[(4-piperidin-1-ylpiperidin-1-yl) methyl]-2-[3-(trifluoromethyl)phenyl]quinoline-4-carboxamide

Chemical Property:

• Boiling Point: 737.8±60.0 °C(Predicted)
• PKA: 12.82±0.20(Predicted)
• Density: 1.43±0.1 g/cm3(Predicted)
• Storage Temp.: room temp
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 690.21811
• Heavy Atom Count: 46
• Complexity: 1020

Purity/Quality:

98%,99%, ^*data from raw suppliers

GSK2193874 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45

MSDS Files:

Useful:

• Canonical SMILES: C1CCN(CC1)C2CCN(CC2)CC3=C(C4=C(C=C(C=C4)Br)N=C3C5=CC(=CC=C5)C(F)(F)F)C(=O)NC6(CC6)C7=CC=CC=C7
• Uses: GSK 2193874 is an orally active, potent and selective TRPV4 antagonist. GSK2193874 has been used as a transient receptor potential vanilloid 4 (TRPV4) antagonist:to study its effects on GSK101-induced colon contractions in miceto study its effects on murine compact bone-derived osteoblasts(CB-OB)to study its effects on lung injury post-lipopolysaccharide (LPS) in mice

Technology Process of 7-bromo-N-(1-phenylcyclopropyl)-3-[(4-piperidin-1-ylpiperidin-1-yl) methyl]-2-[3-(trifluoromethyl)phenyl]quinoline-4-carboxamide

There total 6 articles about 7-bromo-N-(1-phenylcyclopropyl)-3-[(4-piperidin-1-ylpiperidin-1-yl) methyl]-2-[3-(trifluoromethyl)phenyl]quinoline-4-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

3-(1,4'-bipiperidin-1'-ylmethyl)-7-bromo-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (1336964-26-1) + 1-phenylcyclopropylamine (41049-53-0,773012-60-5) → 3-([1,4′-bipiperidin]-1′-ylmethyl)-7-bromo-N-(1-phenylcyclopropyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxamide (1336960-13-4)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 60 ℃; for 5h;

Reference yield:

m-Bromoaniline (591-19-5) → 3-([1,4′-bipiperidin]-1′-ylmethyl)-7-bromo-N-(1-phenylcyclopropyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxamide (1336960-13-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 2 h / 35 - 90 °C

2.1: sulfuric acid / 0.75 h / 65 - 80 °C

2.2: 60 °C

3.1: potassium hydroxide / ethanol; water / 0.25 h

3.2: 18 h / Reflux

3.3: pH 4 - 5

4.1: dibenzoyl peroxide; N-Bromosuccinimide; acetic acid / benzene; tetrachloromethane / 72 h / 100 °C

5.1: acetonitrile / 1 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 5 h / 60 °C

With hydrogenchloride; N-Bromosuccinimide; sulfuric acid; hydroxylamine hydrochloride; benzotriazol-1-ol; acetic acid; sodium sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium hydroxide; dibenzoyl peroxide; In tetrachloromethane; ethanol; dichloromethane; water; acetonitrile; benzene;

Reference yield:

6-bromoisatin (6326-79-0) → 3-([1,4′-bipiperidin]-1′-ylmethyl)-7-bromo-N-(1-phenylcyclopropyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxamide (1336960-13-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hydroxide / ethanol; water / 0.25 h

1.2: 18 h / Reflux

1.3: pH 4 - 5

2.1: dibenzoyl peroxide; N-Bromosuccinimide; acetic acid / benzene; tetrachloromethane / 72 h / 100 °C

3.1: acetonitrile / 1 h / 20 °C

4.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 5 h / 60 °C

With N-Bromosuccinimide; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium hydroxide; dibenzoyl peroxide; In tetrachloromethane; ethanol; dichloromethane; water; acetonitrile; benzene;

upstream raw materials:

m-Bromoaniline

6-bromoisatin

N-(3-bromophenyl)-2-(hydroxyimino)ethanamide

3-(1,4'-bipiperidin-1'-ylmethyl)-7-bromo-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

Refernces

• 1、 -. "TRPV4 ANTAGONISTS". . . Retrieved 2011/10/13.