Hydrochloric Acid → HCID 58547746, compound

HRID 454905Notes

Reaction equation

HRID 454905 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([OH:12])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[OH:38][CH:39]1[CH2:42][NH:41][CH2:40]1.C(N(C(C)C)CC)(C)C.Cl>CN(C=O)C.C(Cl)Cl.CO.O>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]([N:41]1[CH2:42][CH:39]([OH:38])[CH2:40]1)=[O:12]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic acidHCID 27592903-Hydroxyazetidine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58547746HCID 58547746, compoundYield 23.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

1H-benzo[d]imidazole-2-carboxylic acid (1.788 g, 11.03 mmol) was dissolved in 50 ml DMF and HATU (4.19 g, 11.03 mmol) was added. This mixture (A) was stirred for 30 min. 3-hydroxyazetidine hydrochloride (1.2083 g, 11.03 mmol) was added to 50 ml DMF, diisopropylethyl amine (5.76 mL, 33.1 mmol) was added and the mixture (B) was stirred for 5 min. Mixture (B) was added to mixture (A) and the resulting reaction mixture was stirred for 6 hours. The reaction was hydrolyzed with 30 ml water and 30 ml 1M HCl and the resulting mixture was extracted with EtOAc (3×200 ml). The combined organic layers were dried with magnesium sulfate and evaporated. Silica gel chromatography (0-10% MeOH in DCM) provided (1H-benzo[d]imidazol-2-yl)(3-hydroxyazetidin-1-yl)methanone (0.570 g, 2.62 mmol, 23.79% yield) as a yellow oil.

Workup

  1. additionwas added
  2. customthe resulting reaction mixture
  3. extractionthe resulting mixture was extracted with EtOAc (3×200 ml)
  4. dry with materialThe combined organic layers were dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-5409c5184eb544899745c90f4dd6aad3
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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