1-Hydroxybenzotriazole → HCID 86694687, compound

HRID 475235Notes

Reaction equation

HRID 475235 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]([OH:18])=O)=[CH:15][C:10]=2[N:9]=[CH:8]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:42][O:43][NH:44][CH3:45]>C(Cl)Cl.O>[CH3:42][O:43][N:44]([CH3:45])[C:16]([C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[CH:8]=[N:9][C:10]=2[CH:15]=1)=[O:18]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712724931-(Tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 86694687HCID 86694687, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 166 (170 mg, 0.69 mmol) in DCM (5 mL) was added EDC.HCl (190 mg, 1 mmol), HOBt (160 mg, 1 mmol), TEA (0.3 mL) and N-methoxymethanamine hydrochloride (100 mg, 1 mmol). The mixture was stirred at RT overnight. The mixture was poured into water, extracted with EtOAc, washed sequentially with H2O and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography affording 140 mg (85%) of 1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carboxylic acid methoxy-methyl-amide (168) as a light yellow oil.

Workup

  1. extractionextracted with EtOAc
  2. washwashed sequentially with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-95ecdbef2a014afba201df19a16f804e
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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