1-Hydroxybenzotriazole → HCID 69878976, compound

HRID 1838089Notes

Reaction equation

HRID 1838089 reaction equation
CCN=C=NCCCN(C)C.Cl.[C:13]([NH:17][C:18]([C@@H:20]1[C:24]([CH3:26])([CH3:25])[S:23][CH2:22][N:21]1[C:27](=[O:41])[C@@H:28]([OH:40])[C@@H:29]([NH2:39])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH3:42][C:43]1[CH:53]=[CH:52][CH:51]=[C:50]([CH3:54])[C:44]=1[O:45][CH2:46][C:47](O)=[O:48].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[C:13]([NH:17][C:18]([C@@H:20]1[C:24]([CH3:25])([CH3:26])[S:23][CH2:22][N:21]1[C:27](=[O:41])[C@@H:28]([OH:40])[C@@H:29]([NH:39][C:47](=[O:48])[CH2:46][O:45][C:44]1[C:43]([CH3:42])=[CH:53][CH:52]=[CH:51][C:50]=1[CH3:54])[CH2:30][C:31]1[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=1)=[O:19])([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 101369(2,6-Dimethylphenoxy)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69879176HCID 69879176, compound

Product 1

HCID 69878976HCID 69878976, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC-HCl (63 mg) was added to a solution of the compound obtained in Step 2 of Example 17 (127 mg), 2,6-dimethylphenoxyacetic acid (54 mg), and HOBt (41 mg) in DMF, and the mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with 5% Na2CO3 (×2), 1N HCl, and 5% NaCl, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column chromatography and recrystallized from a mixture of EtOAc and n-hexane to obtain the title compound (130 mg).

Workup

  1. washwashed with 5% Na2CO3 (×2), 1N HCl, and 5% NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. customrecrystallized from a mixture of EtOAc and n-hexane

Sources & evidence

ORD record
ord-7541d4ba92154234a29b4a91e7bfa3f5
Source dataset
uspto-grants-2004_01
Patent number
US06673772B2

Reaction notes

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