1-Hydroxybenzotriazole → HCID 67103536, compound

HRID 2080820Notes

Reaction equation

HRID 2080820 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][C:45]=1[NH2:46])[C:41]#[N:42]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C:12](=[O:14])[NH:37][C:38]1[CH:39]=[C:40]([C:41]#[N:42])[CH:43]=[CH:44][C:45]=1[NH2:46])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 7372853,4-DiaminobenzonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67103536HCID 67103536, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A DMF solution (30 ml) containing 4-(t-butoxycarbonylamino)-butyric acid (1.53 g) was added with HOBt (1.07 g) and WSCI hydrochloride (1.51 g) and the whole was stirred for 0.5 hours. The reaction solution was dropped to a DMF solution (12 ml) containing the compound (1.00 g) obtained in Example 46-1. The whole was stirred at room temperature for 12 hours and then the solvent was distilled off. The resultant was dissolved in chloroform, washed with a saturated aqueous ammonium chloride solution and a saturated aqueous sodium hydrogen carbonate solution in the stated order, and dried with anhydrous magnesium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (ethyl acetate/chloroform), thereby obtaining the subject compound (1.57 g) as a milky-white solid.

Workup

  1. stirringThe whole was stirred at room temperature for 12 hours
  2. distillationthe solvent was distilled off
  3. dissolutionThe resultant was dissolved in chloroform
  4. washwashed with a saturated aqueous ammonium chloride solution
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution in the stated order, and dried with anhydrous magnesium sulfate
  6. customThe residue obtained
  7. distillationby distilling the solvent
  8. customoff was purified through silica gel column chromatography (ethyl acetate/chloroform)

Sources & evidence

ORD record
ord-7cf0b9760a614837bf9ec5de6e45455a
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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