1-Hydroxybenzotriazole → HCID 86694687, compound

HRID 475086Notes

Reaction equation

HRID 475086 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.Cl.C(N=C=NCCCN(C)C)C.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 a solution of 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid (170 mg, 0.69 mmol) in DCM (5 mL) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (190 mg, 1 mmol), HOBt (160 mg, 1 mmol), TEA (0.3 mL) and N-methoxy-methanamine hydrochloride (100 mg, 1 mmol). The mixture was stirred at RT overnight. The mixture was poured into water and extracted with EtOAc. The organics were washed sequentially with water and brine, then dried (Na2SO4). Removal of solvent followed by SiO2 chromatography afforded N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carboxamide (140 mg, 85% yield) as a light yellow oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed sequentially with water and brine
  3. dry with materialdried (Na2SO4)
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-ec0a8d0078004d2bba6702cbd26212fa
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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