Water → HCID 66779261, compound

HRID 1470350Notes

Reaction equation

HRID 1470350 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[CH2:25][NH2:26])[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:30](OC(=O)C)(=[O:32])[CH3:31].O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[C:24]([CH2:25][NH:26][C:30](=[O:32])[CH3:31])[CH:27]=[CH:28][CH:29]=3)[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 66779373HCID 66779373, compound

Product 1

HCID 66779261HCID 66779261, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-[2-(3,4,5-Trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzylamine (0.036 mmol) is dissolved in acetic acid (1.00 ml) and acetic acid anhydride (0.159 mmol) is added. The reaction solution is stirred 4 d at RT. Water is added and extracted with ethyl acetate. The combined organic layers are washed with brine and dried over MgSO4. The product is isolated after removal of the solvent in vacuo as yellow solid (45% yield). HPLC (method A): Rt 2.52 min (purity 99.4%); LCMS (ESI+) (method E): Rt 1.87 min, M+H+ 433.1 m/z; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.57 (d, J=5.1, 1H), 8.44 (t, J=5.7, 1H), 8.09 (d, J=12.1, 1H), 7.97 (d, J=7.8, 1H), 7.76 (d, J=2.8, 1H), 7.69-7.56 (m, 2H), 7.44 (t, J=9.5, 1H), 7.33 (d, J=7.8, 2H), 4.39 (d, J=5.9, 2H), 3.91 (d, J=11.1, 6H), 3.78-3.70 (m, 3H), 1.91-1.77 (m, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over MgSO4
  4. customThe product is isolated

Sources & evidence

ORD record
ord-8d40357f7bf648eeae22abb1746b8cbc
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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