Ammonia → HCID 24884914, compound

HRID 11104Notes

Reaction equation

HRID 11104 reaction equation
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][NH:5][C:6](=[O:35])[CH2:7][CH2:8][N:9]1[C:21]2[CH:20]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]3[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:17]=3[C:16]=2[C:15]2[CH:14]=[C:13]([O:33]C)[CH:12]=[CH:11][C:10]1=2.N>O>[CH3:36][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6](=[O:35])[CH2:7][CH2:8][N:9]1[C:21]2[CH:20]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]3[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:17]=3[C:16]=2[C:15]2[CH:14]=[C:13]([OH:33])[CH:12]=[CH:11][C:10]1=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 91425637HCID 91425637, compound

Product 1

HCID 24884914HCID 24884914, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reaction of methyl ether (247) (70 mg, 0.14 mmol) prepared as described in example 207 according to the procedure described in example 81, except that the reaction mixture was diluted with water, basified by the addition of concentrated ammonia and extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetate/methanol/triethylamine (1:0:0 to 3:1:trace). Crystallization from ethyl acetate/hexane then gave amide (254) (35 mg, 53%) as an orange powder, mp 176–180° C. 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.35 (br s, 1H), 8.39 (d, J=2.5 Hz, 1H), 7.77 (s, 1H), 7.74 (t, J=5.6 Hz, 1H), 7.66 (m, 2H), 7.53 (d, J=8.8 Hz, 1H), 7.48 (m, 3H), 7.12 (dd, J=8.8, 2.5 Hz, 1H), 4.69 (t, J=6.4 Hz, 2H), 2.94 (m, 2H), 2.58 (t, J=6.4 Hz, 2H), 1.91 (s, 6H), 1.87 (m, 2H). Found: C, 66.87; H, 5.83; N, 11.47. C27H26N4O4.3/4H2O requires: C, 67.00; H, 5.73; N, 11.57.

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. customthe drying agent was removed
  5. concentrationthe solution was concentrated to dryness
  6. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-63b33118c5334130939d6c3e5f27f1ba
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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