Cyclopentanone → Cyclopentyl-[2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-amine

HRID 336480Notes

Reaction equation

HRID 336480 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15].[C:16]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:16]1([NH:15][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[NH:7][C:6]([C:2]2[S:1][CH2:5][CH2:4][N:3]=2)=[CH:14]3)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 5049666Sodium triacetoxyborohydrideHCID 579017772-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine

Product 1

HCID 44189667Cyclopentyl-[2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-amineYield 34%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

[2-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-amine (15 mg, 0.07 mmol) prepared in Step A was dissolved in 1,2-dichloroethane (10 mL). Cyclopentanone (12 mg, 0.14 mmol) and sodium triacetoxyborohydride (29 mg, 0.14 mmol) were added thereto, and the mixture was stirred for 3 h at room temperature. The reaction was quenched by water, and the reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (6.7 mg, Yield 34%).

Workup

  1. customThe reaction was quenched by water
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-55f703dc3f004045bc09b68703c131a3
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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