2-Benzimidazolecarboxylic acid → HCID 58547470, compound

HRID 1850338Notes

Reaction equation

HRID 1850338 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:11]([Br:12])=[CH:10][N:9]=[C:8]([Cl:13])[N:7]=2)[CH2:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[C:39]1[C:47](O)=[O:48]>C(Cl)Cl>[NH:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[C:39]1[C:47]([N:2]1[CH2:5][CH:4]([C:6]2[C:11]([Br:12])=[CH:10][N:9]=[C:8]([Cl:13])[N:7]=2)[CH2:3]1)=[O:48]

Participants

5

Reactant 3

HCID 2332402-Benzimidazolecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86660170HCID 86660170, compound

Product 1

HCID 58547470HCID 58547470, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-azetidin-3-yl-5-bromo-2-chloro-pyrimidine hydrochloride (0.57 mg, 2.0 mmol) in DCM (20 mL) were added HATU (1.5 g, 4.0 mmol), TEA (404 mg, 4 mmol) and 1H-benzoimidazole-2-carboxylic acid (398 mg, 2.4 mmol). The reaction mixture was stirred at RT for 12 h. TLC showed that most of starting materials were consumed completely. Then the solution was washed with aqueous HCl (1 mol/L) (50 mL×3), saturated aqueous NaHCO3 (50 mL×3) and brine, dried over MgSO4. The solution was evaporated, the residue was purified by column chromatography to give the product (206 mg, 0.53 mmol, yield: 27%). ESI-MS (M+1): 392 calc. for C15H11BrClN5O 391

Workup

  1. customwere consumed completely
  2. washThen the solution was washed with aqueous HCl (1 mol/L) (50 mL×3), saturated aqueous NaHCO3 (50 mL×3) and brine
  3. dry with materialdried over MgSO4
  4. customThe solution was evaporated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-dcb0363bcaca47c9be3934a9537b692e
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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