Diisopropylethylamine → 4-Bromo-1H-indole-2-carboxylic acid [1-(2-azepan-1-yl-ethyl)-piperidin-4-yl]-amide

HRID 2267934Notes

Reaction equation

HRID 2267934 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=O)[NH:6]2.Cl.Cl.Cl.[N:17]1([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[N:17]1([CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][CH:29]([NH:32][C:11]([C:5]3[NH:6][C:7]4[C:3]([CH:4]=3)=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=4)=[O:13])[CH2:30][CH2:31]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 40426044-bromo-1H-indole-2-carboxylic acidHCID 668413931-(2-(Azepan-1-yl)ethyl)piperidin-4-amine trihydrochloride

Product 1

HCID 596002484-Bromo-1H-indole-2-carboxylic acid [1-(2-azepan-1-yl-ethyl)-piperidin-4-yl]-amideYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-1H-indole-2-carboxylic acid (1.5 g, 3.1 mmol), 1-(2-azepan-1-yl-ethyl)-piperidin-4-ylamine tri-hydrochloride (5) (2.1 g, 3.1 mmol) and DIEA (4.3 ml, 12.4 mmol) are dissolved under argon atmosphere in DMF (25 ml). TBTU (2.3 g, 3.4 mmol) is added at room temperature. The reaction mixture is stirred for 2 h at r.t., evaporated under high vacuum, dissolved in ethyl acetate and washed twice with 5% aqueous NaHCO3 solution. The organic layers are dried over sodium sulfate. Evaporation under reduced pressure gave 1.3 g (93%) of a beige solid.

Workup

  1. customevaporated under high vacuum
  2. dissolutiondissolved in ethyl acetate
  3. washwashed twice with 5% aqueous NaHCO3 solution
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-269cfea79be34c13a6c54f18caf50ae9
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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