Dichloromethane → HCID 178522779, compound

HRID 1198974Notes

Reaction equation

HRID 1198974 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH:14]1([CH2:19][NH2:20])[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl.CN(C)CCCN=C=NCC.C(Cl)Cl>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CN(C)C=O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[O:13])[NH:20][CH2:19][CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:8][CH:9]=2)[NH:4][N:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 80153CyclopentanemethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524081HCID 178524081, compound

Product 1

HCID 178522779HCID 178522779, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-bromo-6-carboxyindazole (5.84 g), cyclopentylmethylamine (3.48 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.25 g), methylene chloride (120 ml) and dimethylformamide (40 ml) was added 4-dimethylaminopyridine (5.10 g). After stirring for 48 hours, the reaction mixture was added to 450 ml ethyl acetate; washed with 1N hydrochloric acid, 0.5M sodium carbonate and brine: dried (MgSO4); and evaporated. The residue was flash chromatographed over 175 g silica gel, eluting sequentially with methylene chloride (350 ml), 15:85 ethyl acetate:methylene chloride (350 ml), and 1:3 ethyl acetate:methylene chloride to afford 3-bromo-6-(N-cyclopentylmethylcarbamoyl)indazole as a light red solid (5.6 g, 72%), mp 119°-125°.

Workup

  1. washwashed with 1N hydrochloric acid, 0.5M sodium carbonate and brine
  2. dry with materialdried (MgSO4)
  3. customand evaporated
  4. customchromatographed over 175 g silica gel
  5. washeluting sequentially with methylene chloride (350 ml), 15:85 ethyl acetate

Sources & evidence

ORD record
ord-27a75179488248ca8df2e9176be08bde
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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