Dimethylformamide → HCID 68894597, compound

HRID 1786708Notes

Reaction equation

HRID 1786708 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]([C:17]2[CH:18]=[C:19]([C:23]3[C:24]([C:29]([NH:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:20]=[CH:21][CH:22]=2)[CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:42](OC(=O)NCCN)([CH3:45])([CH3:44])[CH3:43].[CH:53]1[CH:54]=[CH:55][C:56]2N(O)N=N[C:57]=2[CH:58]=1.[CH3:63]CN=C=NCCCN(C)C.CN([CH:77]=[O:78])C>C(=O)(O)[O-].[Na+].C(N(CC)CC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:15]([C:17]2[CH:18]=[C:19]([C:23]3[C:24]([C:29]([NH:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:20]=[CH:21][CH:22]=2)[CH3:16])[C:77](=[O:78])[CH2:45][C:42]2[CH:43]=[CH:63][C:57]3[C:58](=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:44]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 57597465HCID 57597465, compound

Product 1

HCID 68894597HCID 68894597, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the compound obtained in Reference Example 3 (1.20 g) in DMF (40 ml) were added N-(2-aminoethyl)carbamic acid tert-butyl ester (310 mg), HOBt (262 mg) and triethylamine (196 mg). WSC (372 mg) was further added to this mixture under ice-cooling, and the mixture was stirred for 18 hours at room temperature. The obtained reaction mixture was diluted with saturated sodium bicarbonate solution (200 ml), and extracted with ethyl acetate (100 ml) twice. The extracted solutions were combined, washed with saturated brine, dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to give the title compound as a colorless amorphous substance (1.04 g, 74%).

Workup

  1. temperaturecooling
  2. customThe obtained reaction mixture
  3. extractionextracted with ethyl acetate (100 ml) twice
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-246bbab43f254048a1c6b8ae5710095b
Source dataset
uspto-grants-2009_03
Patent number
US07507753B2

Reaction notes

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