Ammonia → HCID 66635626, compound

HRID 709128Notes

Reaction equation

HRID 709128 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[OH:6][CH2:7][CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].N>N1C=CC=CC=1>[CH2:1]([NH:3][C:4](=[O:5])[O:6][CH2:7][CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=1)[CH2:9][NH:10][C:11]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8022Ethyl isocyanate2×HCID 66635640HCID 66635640, compound

Product 1

HCID 66635626HCID 66635626, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5 mg (42 μmol) of 4-N,N-dimethylaminopyridine and 66 μl (0.84 mmol) of ethyl isocyanate were added to a solution of 134 mg (0.42 mmol) of the compound of Example 17A in 2.5 ml of pyridine. The mixture was stirred at RT overnight. A further 66 μl of ethyl isocyanate were then added, and the mixture was heated at 50° C. for 24 h. After cooling to RT, 0.5 ml of ammonia solution (35% in water) was added. The volatile components were removed on a rotary evaporator. A little acetonitrile and 1 N hydrochloric acid were added to the residue, and the solution was separated by preparative HPLC [Method 9]. This gave 110 mg (67% of theory) of the title compound.

Workup

  1. temperaturethe mixture was heated at 50° C. for 24 h
  2. temperatureAfter cooling to RT
  3. customThe volatile components were removed on a rotary evaporator
  4. additionA little acetonitrile and 1 N hydrochloric acid were added to the residue
  5. customthe solution was separated by preparative HPLC [Method 9]

Sources & evidence

ORD record
ord-81a52b2659724d7faa448f297ee5dd4b
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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