Dimethylamine → HCID 58875086, compound

HRID 2355251Notes

Reaction equation

HRID 2355251 reaction equation
C[CH2:2][N:3]=[C:4]=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[C:22]1([S:28]([NH:31][C:32]2[CH:33]=[C:34]([C@@H:38]([OH:58])[CH2:39][NH:40][C:41]([CH3:57])([CH3:56])[CH2:42][CH2:43][N:44]3[C:52]4[C:47](=CC(C(O)=O)=C[CH:51]=4)[CH:46]=[CH:45]3)[CH:35]=[CH:36][CH:37]=2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C.CNC.[CH2:71]1[CH2:75][O:74][CH2:73][CH2:72]1>CN(C=O)C>[CH3:2][N:3]([CH3:4])[C:73]([C:72]1[CH:71]=[C:75]2[C:45](=[CH:46][CH:47]=1)[N:44]([CH2:43][CH2:42][C:41]([NH:40][CH2:39][C@@H:38]([C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([NH:31][S:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:29])=[O:30])[CH:33]=1)[OH:58])([CH3:56])[CH3:57])[CH:52]=[CH:51]2)=[O:74]

Participants

8

Reactant 6

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16660493HCID 16660493, compound

Product 1

HCID 58875086HCID 58875086, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDCI (75 mg, 0.39 mmol) and HOBt (49 mg, 0.36 mmol) are added to a solution of 1-{3-[(R)-2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylic acid-hydrotrifluoroacetate (Example 6; 100 mg, 0.16 mmol) in 2 ml DMF. Then the reaction mixture is stirred for 60 minutes at RT and combined with DIPEA (66 μl, 0.39 mmol). After 10 minutes stirring at RT a solution of dimethylamine in THF (2.0M; 2.5 ml, 5.0 mmol) is added. After 22 hours stirring at RT the solvent is eliminated in vacuo and the residue is chromatographed on Microsorb C18-reverse-phase [acetonitrile (0.1% TFA)/water (0.13% TFA)=10:90→100:0]. After freeze-drying the salt is converted into the base in ethyl acetate with semisaturated sodium hydrogen carbonate solution.

Workup

  1. additionis added
  2. stirringAfter 22 hours stirring at RT the solvent
  3. customthe residue is chromatographed on Microsorb C18-reverse-phase [acetonitrile (0.1% TFA)/water (0.13% TFA)=10:90→100:0]
  4. customAfter freeze-drying the salt

Sources & evidence

ORD record
ord-4406ffc3bf0e4eb49dd2d6c7c0ebe689
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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