Water → HCID 58303937, compound

HRID 1404120Notes

Reaction equation

HRID 1404120 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH2:10][CH2:11][C:12]1[C:13]([O:30][CH3:31])=[C:14]2[C:18](=[C:19]([F:21])[CH:20]=1)[N:17]([CH2:22][CH3:23])[CH:16]=[C:15]2[CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26].O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[CH2:10][CH2:11][C:12]1[C:13]([O:30][CH3:31])=[C:14]2[C:18](=[C:19]([F:21])[CH:20]=1)[N:17]([CH2:22][CH3:23])[CH:16]=[C:15]2[CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 58303989HCID 58303989, compound

Product 1

HCID 58303937HCID 58303937, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 29-2 (230 mg, 0.52 mmol) in acetic acid (10 mL) was heated to 80° C. for 3 h. After cooled to room temperature, water (10 mL) and sat. aqueous NaHCO3 (30 mL) were added. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried with MgSO4, filtered and evaporated to afford 29-3 (150 mg, 68%) as yellow oil. LRMS: calc 422.5 and found: 423.2 [M+1].

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic layer was dried with MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f38bcb6561714dbc943a52c2885294a5
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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