1-Hydroxybenzotriazole → HCID 69878533, compound

HRID 1838090Notes

Reaction equation

HRID 1838090 reaction equation
CCN=C=NCCCN(C)C.Cl.[CH3:13][C:14]1[CH:45]=[CH:44][CH:43]=[CH:42][C:15]=1[CH2:16][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].[NH2:46][C:47]1[C:48]([CH3:56])=[C:49]([CH:53]=[CH:54][CH:55]=1)[C:50](O)=[O:51].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[CH3:13][C:14]1[CH:45]=[CH:44][CH:43]=[CH:42][C:15]=1[CH2:16][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]([NH:39][C:50](=[O:51])[C:49]1[CH:53]=[CH:54][CH:55]=[C:47]([NH2:46])[C:48]=1[CH3:56])[CH2:30][C:31]1[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=1)=[O:19]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27336993-Amino-2-methylbenzoic acidHCID 69879159HCID 69879159, compound

Product 1

HCID 69878533HCID 69878533, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC.HCl (42 mg) was added to a solution of the compound obtained in Step 2 of Example 1 (94 mg), 3-amino-2-methylbenzoic acid (30 mg), and HOBt (27 mg) in DMF while cooling with ice, and the mixture was stirred overnight. EtOAc was added and the mixture was washed with 5% Na2CO3 (×2) and 5% NaCl, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2—MeOH) and reprecipitated from a mixture of CH2Cl2 and n-hexane to obtain the title compound (77 mg, 64%).

Workup

  1. temperaturewhile cooling with ice
  2. washthe mixture was washed with 5% Na2CO3 (×2) and 5% NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (CH2Cl2—MeOH)
  7. customreprecipitated from a mixture of CH2Cl2 and n-hexane

Sources & evidence

ORD record
ord-0c08a5a880644af880251066c53f0961
Source dataset
uspto-grants-2004_01
Patent number
US06673772B2

Reaction notes

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