HCID 10341299, compound → HCID 67104278, compound

HRID 273253Notes

Reaction equation

HRID 273253 reaction equation
C(OC([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[C:18]([CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][C@H:26]3[CH3:30])[N:19]=[N:20]2)=[CH:15][CH:14]=1)=O)(C)(C)C.C[O-].[Na+]>O1CCCC1>[CH3:30][C@@H:26]1[CH2:27][CH2:28][CH2:29][N:25]1[CH2:24][CH2:23][C:18]1[N:19]=[N:20][C:21]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:9]1[NH:8][CH:12]=[CH:11][CH:10]=1)[CH:22]=2

Participants

4

Reactant 2

HCID 10341299HCID 10341299, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 67104278HCID 67104278, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 187 (0.007 g, 0.017 mmol) in tetrahydrofuran (2 mL), was added NaOMe (0.03 mL, 25% in methanol) and stirred at r.t. for 3 hours. The reaction mixture was then concentrated under reduced pressure, re-dissolved in water (2 mL), extracted with ethyl acetate (2 mL), dried with Na2SO4, and concentrated to afford the product in 76% yield as a yellowish solid. 1H NMR (CD3OD, 300 MHz) δ 8.31 (m, 1H), 8.02 (dd, J=3, 9 Hz, 1H), 7.90 (s, 1H), 7.79 (d, J=9 Hz, 1H), 6.89 (m, 1H), 6.71 (m, 1H), 6.18 (m, 1H), 3.33-3.19 (m, 4H), 2.53-2.22 (m, 3H), 1.96-1.87 (m, 1H), 1.77-1.64 (m, 2H), 1.43-1.37 (m, 1H), 1.06 (d, J=6 Hz, 3H). MS (ESI) [M+H]+ at 307.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionre-dissolved in water (2 mL)
  3. extractionextracted with ethyl acetate (2 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customto afford the product in 76% yield as a yellowish solid

Sources & evidence

ORD record
ord-644d2395bff74c2dbc5fe26b811fc38b
Source dataset
uspto-grants-2008_11
Patent number
US07456196B2

Reaction notes

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