1-Hydroxybenzotriazole → HCID 21904700, compound

HRID 1246613Notes

Reaction equation

HRID 1246613 reaction equation
C1C=CC2N(O)N=[N:7]C=2C=1.[CH3:11][N:12]([CH2:14][C:15]1[C:16]([O:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)=[N:17][CH:18]=[C:19]([CH:23]=1)[C:20]([OH:22])=O)[CH3:13]>C(Cl)Cl>[CH3:11][N:12]([CH2:14][C:15]1[C:16]([O:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][C:32]([F:33])([F:34])[F:35])=[CH:29][CH:30]=2)=[N:17][CH:18]=[C:19]([CH:23]=1)[C:20]([NH2:7])=[O:22])[CH3:13]

Participants

4

Reactant 2

HCID 757711-HydroxybenzotriazoleHCID 21904716HCID 21904716, compound

Product 1

HCID 21904700HCID 21904700, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-N-Diisopropylethylamine (44 μL, 0.25 mmol), HOBt (20 mg, 0.15 mmol) and WSCDI (23 mg, 0.12 mmol) were added to the acid from step (i) (35 mg, 0.10 mmol) in CH2Cl2 (2 mL) and stirred for 30 min. (NH4)2CO3 (19 mg, 0.20 mmol) was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was partitioned between water (10 mL) and CH2Cl2 (10 mL) and the organic layer was dried (MgSO4) and evaporated. The residue was purified by column chromatography [SiO2; DCM/MeOH/880 NH3 (93:7:1)] and then triturated with Et2O to give the desired product (20 mg, 57%) as a white solid; δH (CDCl3, 400 MHz) 2.35 (6H, s), 3.62 (2H, s), 5.66 (1H, br), 6.00 (1H, br), 7.18 (2H, m), 7.26 (2H, m), 8.23 (1H, d), 8.50 (1H, d); MS m/z (TS+) 356 (MH+).

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between water (10 mL) and CH2Cl2 (10 mL)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography [SiO2; DCM/MeOH/880 NH3 (93:7:1)]
  6. customtriturated with Et2O

Sources & evidence

ORD record
ord-23d36a70b7434b068f5e8917ce4fd5c7
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Reaction notes

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