Acetic Anhydride → HCID 59577666, compound

HRID 1947517Notes

Reaction equation

HRID 1947517 reaction equation
Cl.Cl.[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[O:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]3)=[CH:18][NH:19]2)=[CH:15][CH:14]=1.CCN(CC)CC.[C:37](OC(=O)C)(=[O:39])[CH3:38]>C(Cl)Cl>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[O:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([NH:29][C:37](=[O:39])[CH3:38])[CH2:25][CH2:24]3)=[CH:18][NH:19]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68771881HCID 68771881, compound

Product 1

HCID 59577666HCID 59577666, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-[6-(benzothiazol-2-yloxy)-1H-indol-3-ylmethyl]-piperidin-4-ylamine 2HCl (200 mg, 0.44 mmol) in DCM (4 mL) was added Et3N (0.37 mL, 270 mg, 2.7 mmol) and acetic anhydride (0.067 mL, 68 mg, 0.66 mmol) and the resulting reaction mixture was stirred (rt, 24 h). The reaction mixture was partitioned with EtOAc (50 mL) and brine (50 mL) and the organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified silica gel flash column chromatography using MeOH (0.2 M NH3):DCM (0-15%) to provide the title compound as a white solid (111 mg, 60%). MS (ESI): mass calcd. for C23H24N4O2S, 420.5; m/z found, 421.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.00 (s, 1H), 7.73 (d, J=6.0, 1H), 7.71 (d, J=5.2, 1H), 7.63 (d, J=7.5, 1H), 7.39-7.36 (m, 1H), 7.31 (br s, 1H), 7.26-7.24 (m, 1H), 7.10 (br s, 1H), 7.07 (dd, J=8.6, 2.1, 1H), 5.55 (br d, 1H), 3.80-3.70 (m, 1H), 3.68 (s, 2H), 2.89 (d, J=11.7, 2H), 2.17-2.13 (m, 2H), 1.96 (s, 3H), 1.89 (d, J=11.0, 2H), 1.48-1.40 (m, 2H).

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was partitioned with EtOAc (50 mL) and brine (50 mL)
  3. customthe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified silica gel flash column chromatography

Sources & evidence

ORD record
ord-e05350c61e6b44a392b7fc235d4fa1cc
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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