Diisopropylethylamine → HCID 66841918, compound

HRID 1929194Notes

Reaction equation

HRID 1929194 reaction equation
N1([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[C:25]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:12][CH2:11]2)CCCCCC1.C(N1CCC(N)CC1)[C:34]1[CH:39]=[CH:38]C=[CH:36][CH:35]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH2:9]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[C:25]([O:28][CH2:29][CH:30]([CH3:31])[CH3:32])[CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:12][CH2:11]1)[C:8]1[CH:38]=[CH:39][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 114420474-Isobutoxy-1H-indole-2-carboxylic acid [1-(2-azepan-1-yl-ethyl)-piperidin-4-yl]-amide

Product 1

HCID 66841918HCID 66841918, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Isobutoxy-1H-indole-2-carboxylic acid 80 (4.7 g, 20.1 mmol, preparation see Example 8) and 1-benzyl-piperidin-4-ylamine (4.2 ml, 20.1 mmol) are dissolved in 70 ml of DMF and after addition of TBTU (7.3 g, 22.1 mmol) and ethyldiisopropylamine (13.8 ml, 80.4 mmol) the mixture is stirred at room temperature for 2 h. Then the solvent is evaporated at high vacuum. The residue is dissolved in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine. The organic layers are dried over sodium sulfate and evaporated under reduced pressure.

Workup

  1. customThen the solvent is evaporated at high vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b3c327df451046d6a740dabb6d1e6ebb
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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