N,1-dimethylpyrrolidin-3-amine → HCID 178480456, compound

HRID 77102

Reaction equation

HRID 77102 reaction equation
Cl.[Cl:2][C:3]1[CH:27]=[CH:26][C:6]2[NH:7][C:8]([C:10]3[CH:11]=[C:12]([N:17]4[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=O)[CH2:19][CH2:18]4)[CH:13]=[CH:14][C:15]=3[F:16])=[N:9][C:5]=2[CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:52][NH:53][CH:54]1[CH2:58][N:57]([CH3:59])[CH2:56][CH2:55]1>>[CH3:52][N:53]([CH:54]1[CH2:55][CH2:56][N:57]([CH3:59])[CH2:58]1)[C:23]([CH:20]1[CH2:21][CH2:22][N:17]([C:12]2[CH:13]=[CH:14][C:15]([F:16])=[C:10]([C:8]3[NH:7][C:6]4[CH:26]=[CH:27][C:3]([Cl:2])=[CH:4][C:5]=4[N:9]=3)[CH:11]=2)[CH2:18][CH2:19]1)=[O:25]

Participants

4

Reactant 3

HCID 2758520N,1-dimethylpyrrolidin-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178479749HCID 178479749, compound

Product 1

HCID 178480456HCID 178480456, compoundYield 30%

Conditions

Temperature
35 °C

Procedure

Method J—Step a To a mixture of 1-[3-(5-Chloro-1H-benzoimidazol-2-yl)-4-fluoro-phenyl]-piperidine-4-carboxylic acid hydrochloride (obtained as described in general method 10, step b) (0.01 g, 0.25 mmol) in dcm (2 mL), HATU (0.10 g, 0.26 mmol), TEA (0.07 mL, 0.55 mmol) and N,N′-dimethyl-3-aminopyrrolidine (0.04 g, 0.31 mmol) were added. The reaction mixture was heated at 35° C. overnight, cooled to room temperature and washed with ammonium chloride solution (2 mL), saturated Na2CO3 solution (2 mL) and water (2 mL). The organic layer was then filtrated on an NH2 cartridge and further purified by flash chromatography (eluent: EtOAc:NH3 2N in MeOH/9:1) to obtain 0.03 g of the title compound (30%).

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. washwashed with ammonium chloride solution (2 mL), saturated Na2CO3 solution (2 mL) and water (2 mL)
  4. filtrationThe organic layer was then filtrated on an NH2 cartridge
  5. customfurther purified by flash chromatography (eluent: EtOAc:NH3 2N in MeOH/9:1)

Sources & evidence

ORD record
ord-5a847595c8984844a698703d86c9781a
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Linked notes

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