1-Hydroxybenzotriazole → HCID 16727971, compound

HRID 1596320Notes

Reaction equation

HRID 1596320 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([O:11][CH2:12][C:13]([OH:15])=O)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:38][C:39]1[CH:75]=[CH:74][CH:73]=[CH:72][C:40]=1[CH2:41][NH:42][C:43]([C@@H:45]1[C:49]([CH3:51])([CH3:50])[S:48][CH2:47][N:46]1[C:52](=[O:71])[C@@H:53]([OH:70])[C@@H:54]([NH:62][C:63](=[O:69])[C@H:64]([CH:66]([CH3:68])[CH3:67])[NH2:65])[CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)=[O:44]>C(OCC)(=O)C>[CH3:38][C:39]1[CH:75]=[CH:74][CH:73]=[CH:72][C:40]=1[CH2:41][NH:42][C:43]([C@@H:45]1[C:49]([CH3:51])([CH3:50])[S:48][CH2:47][N:46]1[C:52](=[O:71])[C@@H:53]([OH:70])[C@@H:54]([NH:62][C:63](=[O:69])[C@H:64]([CH:66]([CH3:68])[CH3:67])[NH:65][C:13](=[O:15])[CH2:12][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]=[CH:1]2)[CH2:55][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)=[O:44]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 129027902-(Isoquinolin-5-yloxy)acetic acidHCID 20686737HCID 20686737, compound

Product 1

HCID 16727971HCID 16727971, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-isoquinolinyloxyacetic acid (64 mg), HOBt (43 mg), and EDC.HCl (60 mg) were added to H-Val-Apns-Dmt-NHBzl(2-Me) (162 mg) obtained in the step 2 and the mixture was stirred overnight. After the addition of ethyl acetate, the reaction mixture was washed with 3% NaHCO3 and 5% NaCl and dried over MgSO4. After filtration and concentration, the residue was reprecipitated from ethyl acetate/n-hexane to obtain the title compound (168 mg).

Workup

  1. customobtained in the step 2
  2. washthe reaction mixture was washed with 3% NaHCO3 and 5% NaCl
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was reprecipitated from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-6aacf038040140568c07055b5f8591d5
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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