Diisopropylethylamine → 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-indole-5-carboxylic acid methyl ester

HRID 460002Notes

Reaction equation

HRID 460002 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([OH:16])=O)=[CH:8]2)=[O:4].Cl.[CH:18]([N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)([CH3:20])[CH3:19].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14](=[O:16])[NH:27][CH:24]1[CH2:25][CH2:26][N:21]([CH:18]([CH3:20])[CH3:19])[CH2:22][CH2:23]1)=[CH:8]2)=[O:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 230334601-Isopropylpiperidin-4-amine hydrochlorideHCID 529879165-(methoxycarbonyl)-1H-indole-2-carboxylic acid

Product 1

HCID 685586112-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-indole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg 1H-Indole-2,5-dicarboxylic acid 5-methyl ester and 491 mg 1-Isopropyl-piperidin-4-ylamine hydrochloride in 20 ml absolute DMF, 746 mg TOTU and 1.1 ml DIPEA were added and the mixture was stirred at RT for 2 h. The solvent was removed in vacuo and the residue was directly purified by chromatography on silica gel eluting with a gradient of DCM/MeOH 100%->60%. The fractions containing the product were combined and the solvent evaporated under reduced ressure. Yield: 0.73 g.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was directly purified by chromatography on silica gel eluting with a gradient of DCM/MeOH 100%->60%
  3. additionThe fractions containing the product
  4. customthe solvent evaporated under reduced ressure

Sources & evidence

ORD record
ord-af494b5f34704b5d89c7b0fbc0a64e0c
Source dataset
uspto-grants-2007_03
Patent number
US07196103B2

Reaction notes

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