1-Hydroxybenzotriazole → HCID 118275128, compound

HRID 2205673Notes

Reaction equation

HRID 2205673 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:37][CH:38]([C:48]1[O:49][C:50]([C:53]2[C:54](=[O:64])[N:55]([CH3:63])[C:56]3[C:61]([CH:62]=2)=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:51][N:52]=1)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](=[O:47])[CH2:45][CH3:46]>CN(C=O)C.C(Cl)Cl>[CH3:63][N:55]1[C:56]2[C:61](=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:62]=[C:53]([C:50]2[O:49][C:48]([C@@H:38]([NH:37][C:12]([CH:10]3[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:11]3)=[O:14])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](=[O:47])[CH2:45][CH3:46])=[N:52][CH:51]=2)[C:54]1=[O:64]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 90036338HCID 90036338, compound

Product 1

HCID 118275128HCID 118275128, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (1.3 eq), HOBt (1.3 eq) and EDC.HCl (1.3 eq) in DMF (premixed for 10 min) was added to S)-3-(2-(1-amino-7-oxononyl)oxazol-5-yl)-1-methylquinolin-2(1 H)-one (1 eq), obtained as described above. The mixture was stirred o/n at room temperature. The reaction mixture was diluted with DCM, washed with sat. aq. NaHCO3 solution, brine, dried (Na2SO4), filtered and concentrated. The mixture was purified by flash chromatography on silica, eluting with EtOAc/petroleum ether (from 50% of EtOAc to 100% of EtOAc). MS (ES) C31H40N4O6 requires: 564.67, found: 565.

Workup

  1. customobtained
  2. washwashed with sat. aq. NaHCO3 solution, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture was purified by flash chromatography on silica
  7. washeluting with EtOAc/petroleum ether (from 50% of EtOAc to 100% of EtOAc)

Sources & evidence

ORD record
ord-b6bdfe8cbc70407abb10893fa5a5884c
Source dataset
uspto-grants-2016_06
Patent number
US09371295B2

Reaction notes

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