Ammonia → HCID 58959127, compound

HRID 915872Notes

Reaction equation

HRID 915872 reaction equation
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@@H:12]3[O:22][C@H:21]([CH2:23][O:24]C(=O)C)[C@@H:16]([O:17]C(=O)C)[C@H:13]3[O:14][CH3:15])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:28]>CO>[NH2:28][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@@H:12]3[O:22][C@H:21]([CH2:23][OH:24])[C@@H:16]([OH:17])[C@H:13]3[O:14][CH3:15])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58959113HCID 58959113, compound

Product 1

HCID 58959127HCID 58959127, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-55 °C

Procedure

A solution of compound 5.6 (28.8 mg, 0.057 mmol) in MeOH (3 mL) was transferred to a steel bomb, cooled to −50 to −60° C., and treated with a saturated solution of ammonia in MeOH (10 mL). The reactor was sealed and heated at 118° C. overnight. The reaction vessel was cooled (0-5° C.), opened carefully and the reaction mixture was evaporated to dryness. The crude product was dissolved in MeOH, adsorbed onto silica gel and purified by flash column chromatography on silica gel using pure CH2Cl2 to 4% MeOH in CH2Cl2 as eluents to give the desired compound 5.7 (20.7 mg) as an off white solid.

Workup

  1. customThe reactor was sealed
  2. temperatureheated at 118° C. overnight
  3. temperatureThe reaction vessel was cooled (0-5° C.)
  4. customthe reaction mixture was evaporated to dryness
  5. dissolutionThe crude product was dissolved in MeOH
  6. custompurified by flash column chromatography on silica gel using pure CH2Cl2 to 4% MeOH in CH2Cl2 as eluents

Sources & evidence

ORD record
ord-86b4c128ddb3478b8d12a93997e78cc7
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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