Urea → HCID 19829859, compound

HRID 1493638Notes

Reaction equation

HRID 1493638 reaction equation
C[O-].[Na+].NC(N)=O.[NH2:8][C:9]([NH:11][N:12]([CH2:28][C:29]([O:31]C)=O)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:14]=1)=[O:10]>CO>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:15]2[CH:14]=[C:13]([N:12]3[CH2:28][C:29](=[O:31])[NH:8][C:9](=[O:10])[NH:11]3)[CH:18]=[CH:17][CH:16]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 10942334Sodium MethoxideHCID 54104674HCID 54104674, compound

Product 1

HCID 19829859HCID 19829859, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (467 mg, 8.6 mmol) was added to a stirred solution of the urea (Intermediate 80, 1 g, 2.88 mmol) in methanol (40 ml) and the mixture was stirred at 20°-25° for 2 h. The mixture was poured into pH6.7 buffer (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (2×100 ml) and brine (100 ml) before drying (Na2SO4) and evaporating in vacuo to a yellow solid. Trituration with ether gave the title compound as a white solid (265 mg, 29%) m.p. 185°-187° (dec).

Workup

  1. additionThe mixture was poured into pH6.7 buffer (100 ml)
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined extracts were washed with water (2×100 ml) and brine (100 ml)
  4. dry with materialbefore drying (Na2SO4)
  5. customevaporating in vacuo to a yellow solid

Sources & evidence

ORD record
ord-485e38e356514ffdbe24e39eab533f97
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

Loading…