1-Butanol → HCID 58547720, compound

HRID 2207800Notes

Reaction equation

HRID 2207800 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[C:11]([Cl:12])=[N:10][CH:9]=[CH:8][N:7]=2)[CH2:2]1.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:22](O)=[O:23].CCN=C=NCCCN(C)C.C(O)CCC.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:22]([N:1]1[CH2:2][CH:3]([O:5][C:6]2[C:11]([Cl:12])=[N:10][CH:9]=[CH:8][N:7]=2)[CH2:4]1)=[O:23]

Participants

7

Reactant 5

HCID 2631-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic acidHCID 58547920HCID 58547920, compound

Product 1

HCID 58547720HCID 58547720, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(azetidin-3-yloxy)-3-chloropyrazine (see PREPARATION P22.1; 0.38 g, 2.047 mmol), 1H-benzo[d]imidazole-2-carboxylic acid (0.37 g, 2.282 mmol), EDCI (0.392 g, 2.047 mmol), butanol (0.121 g, 0.790 mmol) and DCM (25 mL) was added DIPEA (0.62 mL, 3.56 mmol). After 2 hours, the crude reaction was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with 0% to 50% EtOAc in hexane, to provide (1H-benzo[d]imidazol-2-yl)(3-(3-chloropyrazin-2-yloxy)azetidin-1-yl)methanone (270 mg, 0.819 mmol, 40.0% yield), as a white solid. MS (ESI) m/z 330.0 (MH+). IC50 (uM) 1.375.

Workup

  1. customthe crude reaction
  2. customchromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  3. washeluting with 0% to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-fa646d276bce45f6866c575c4aa5348f
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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