Acetic Anhydride → HCID 68405241, compound

HRID 1771074Notes

Reaction equation

HRID 1771074 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[C:8]2[CH:21]=[CH:22][CH:23]=[CH:24][C:7]=2[N:6]=1.CCN(CC)CC.[CH3:32][C:33](OC(C)=O)=[O:34]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:33]([NH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)[C:8]2[CH:21]=[CH:22][CH:23]=[CH:24][C:7]=2[N:6]=1)(=[O:34])[CH3:32]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68405519HCID 68405519, compound

Product 1

HCID 68405241HCID 68405241, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottom flask charged with methyl 4-((2-(3-aminopropyl)-1H-benzo[d]imidazol-1-yl)methyl)benzoate 34 (135 mg, 0.417 mmol) in DCM (5 mL) was added Et3N (0.076 mL, 0.543 mmol) and catalytic DMAP (5 mg, 0.042 mmol). The reaction was cooled to 0° C. and then Ac2O (0.051 mL, 0.543 mmol) was added dropwise. The resulting solution was allowed to warm to RT and stirred for 18 h after which the reaction was quenched with H2O (10 mL) and extracted with chloroform (3×10 mL). Combined extracts were washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo. The crude product was purified using automated column chromatography method 2 and isolated as a white, waxy solid (53 mg, 35%). 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=8.0 Hz, 2H), 7.73 (d, J=7.6 Hz, 1H), 7.24 (m, 3H), 7.07 (d, J=8.0 Hz, 2H), 6.73 (br s, 1H), 5.38 (s, 2H), 3.88 (s, 3H), 3.33 (m, 2H), 2.89 (t, J=7.2H, 2H), 2.05 (m, 2H), 1.86 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 170.44, 166.32, 154.48, 141.76, 140.60, 134.98, 130.26, 129.91, 126.00122.81, 122.49, 118.89, 109.42, 52.12, 46.60, 38.91, 26.42, 24.92, 22.97. ESI-LRMS: [M+H]+=366 m/z.

Workup

  1. temperatureto warm to RT
  2. customwas quenched with H2O (10 mL)
  3. extractionextracted with chloroform (3×10 mL)
  4. washCombined extracts were washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-dc6906800e884153af6fe0c190ac385e
Source dataset
uspto-grants-2016_02
Patent number
US09249087B2

Reaction notes

Loading…