HCID 69260969, compound → HCID 16665624, compound

HRID 2366450Notes

Reaction equation

HRID 2366450 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:10])[NH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[CH:33]=[CH:32][C:17]([CH2:18][CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)=[CH:16][CH:15]=1)=O>C(O)(=O)C>[NH:22]1[CH2:21][CH2:20][CH:19]([CH2:18][C:17]2[CH:16]=[CH:15][C:14]([C:12]3[NH:11][C:3]4[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([NH2:9])=[O:10])[C:2]=4[N:1]=3)=[CH:33][CH:32]=2)[CH2:24][CH2:23]1

Participants

3

Reactant 1

HCID 69260969HCID 69260969, compound

Product 1

HCID 16665624HCID 16665624, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of EXAMPLE 20A in acetic acid at reflux was stirred for 2 hours, cooled and concentrated. The concentrate was dissolved in ethyl acetate, washed with sodium bicarbonate and water and concentrated. The concentrate was flash chromatographed on silica gel with 20% Methanol/ethyl acetate. 1H NMR (DMSO-d6) δ 1.27-1.44 (m, 2H), 1.75 (d, J=13.20 Hz, 2H), 1.82-1.97 (m, 1H), 2.65 (d, J=7.06 Hz, 2H), 2.76-2.92 (m, 2H), 3.26 (d, J=12.89 Hz, 2H), 7.35 (t, J=7.83 Hz, 1H), 7.42 (d, J=8.29 Hz, 2H), 7.74 (d, J=0.92 Hz, 1H), 7.76 (d, J=0.92 Hz, 1H), 7.87 (d, J=6.75 Hz, 1H), 8.18 (d, J=8.29 Hz, 2H), 8.25 (d, J=7.98 Hz, 1H), 8.55 (d, J=11.97 Hz, 1H), 9.26 (s, 1H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in ethyl acetate
  4. washwashed with sodium bicarbonate and water
  5. concentrationconcentrated
  6. customchromatographed on silica gel with 20% Methanol/ethyl acetate

Sources & evidence

ORD record
ord-ca375f7694a74d75a16bd8b7f41c79c1
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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