Triethylamine → Methyl 4-chloro1-(3-hydroxypropyl)-2-[(2-methoxy-4,6-dimethylpyrimidin-5-yl)amino]-1H-benzimidazole-7-carboxylate

HRID 1628500Notes

Reaction equation

HRID 1628500 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])[C:3]=1[NH:17][C:18](=S)[NH:19][C:20]1[C:21]([CH3:29])=[N:22][C:23]([O:27][CH3:28])=[N:24][C:25]=1[CH3:26].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:3]2[N:17]=[C:18]([NH:19][C:20]3[C:21]([CH3:29])=[N:22][C:23]([O:27][CH3:28])=[N:24][C:25]=3[CH3:26])[N:12]([CH2:13][CH2:14][CH2:15][OH:16])[C:4]=2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86632892Methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-{[(2-methoxy-4,6-dimethylpyrimidin-5-yl)carbamothioyl]amino}benzoate

Product 1

HCID 68760563Methyl 4-chloro1-(3-hydroxypropyl)-2-[(2-methoxy-4,6-dimethylpyrimidin-5-yl)amino]-1H-benzimidazole-7-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-{[(2-methoxy-4,6-dimethylpyrimidin-5-yl)carbamothioyl]amino}benzoate (13.1 g, 28.9 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.10 g, 31.8 mmol), and triethylamine (4.4 mL) in tetrahydrofuran (96 mL) was stirred at 60° C. for 2 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with tetrahydrofuran/ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with ethyl acetate/diisopropyl ether to give the title compound as a pale yellow powder (11.9 g, 28.3 mmol, 98%).

Workup

  1. extractionextracted with tetrahydrofuran/ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-4248f108898844adb830a2c6a8964408
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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