Triethylamine → HCID 178502905, compound

HRID 1842505Notes

Reaction equation

HRID 1842505 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([CH:9]3[CH2:12][N:11]([C:13]4N=CC=[CH:18][C:14]=4[C:15](O)=[O:16])[CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[NH:24]1C[CH:26]([OH:28])[CH2:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([C:9]3([CH:10]4[CH:26]([OH:28])[CH2:25][NH:24]4)[CH:18]=[CH:14][CH:13]=[N:11][CH2:12]3)=[N:8][C:4]=2[CH:3]=1.[CH2:15]=[O:16]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 15142903-HydroxyazetidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524455HCID 178524455, compound

Product 1

HCID 178502905HCID 178502905, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[3-(5-chloro-1H-benzoimidazol-2-yl)-azetidin-1-yl]-nicotinic acid (100 mg, 0.30 mmol), azetidin-3-ol (200 mg, 2.73 mmol), HATU (347 mg, 0.9 mmol), and Et3N (101 mg, 1 mmol) in dry DCM (10 mL) was stirred at RT overnight. The mixture was then poured into saturated aqueous Na2CO3. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the crude compound which was purified by column chromatography and followed by preparative HPLC to afford pure product {2-[3-(5-chloro-1H-benzoimidazol-2-yl]-pyridin-3-yl}-(3-hydroxy-azetidin)-methanone (30 mg, yield 30%). [M+1] 384. IC50 (uM) 0.549.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give the crude compound which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-905fbf55526d4989a5d35e9fadfaa013
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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