Triethylamine → HCID 59376011, compound

HRID 661502Notes

Reaction equation

HRID 661502 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:5](=[O:14])[CH2:6][CH2:7][CH2:8][C:9]=2[C:10]=1[C:11]([OH:13])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[NH2:43][CH2:44][CH:45]([OH:52])[CH2:46][N:47]([CH2:50][CH3:51])[CH2:48][CH3:49]>CN(C=O)C>[CH2:48]([N:47]([CH2:50][CH3:51])[CH2:46][CH:45]([OH:52])[CH2:44][NH:43][C:11]([C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:14])[C:4]=2[NH:3][C:2]=1[CH3:1])=[O:13])[CH3:49]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 977491-Amino-3-(diethylamino)propan-2-olHCID 59376005HCID 59376005, compound

Product 1

HCID 59376011HCID 59376011, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (S4) 0.2 g (1.0 mmol), HOBt 0.16 g (1.2 mmol), EDCI 0.24 g (1.2 mmol) and triethylamine 0.2 g (2.0 mmol) in 10 ml DMF was stirred at room temperature for 20 min, then 1-amino-3-(diethylamino)propan-2-ol 0.31 g (2.1 mmol) was added. After stirred at room temperature for 24 hours, the mixture was poured into the ice water and extracted with CH2Cl2. The organic layer separated was washed with water and saturated sodium chloride solution, then dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column, eluted with CH2Cl2/MeOH (3:1), to give 0.26 g (81%) of the titled compound as a white solid.

Workup

  1. stirringAfter stirred at room temperature for 24 hours
  2. extractionextracted with CH2Cl2
  3. customThe organic layer separated
  4. washwas washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column
  8. washeluted with CH2Cl2/MeOH (3:1)

Sources & evidence

ORD record
ord-66363e614246499fa6294856e88a3cad
Source dataset
uspto-grants-2011_12
Patent number
US08084621B2

Reaction notes

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