Methanol → HCID 22479683, compound

HRID 2183127Notes

Reaction equation

HRID 2183127 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH:15][CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=O)=[O:14])=[CH:10][CH:11]=2)[C:6]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[N:5]1)(=O)C.CO.[OH-].[NH4+:35].C([O-])(=O)C.[NH4+]>CN(C)C=O>[C:18]([CH2:17][CH2:16][NH:15][C:13]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][N:5]=[C:6]2[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)=[O:14])(=[O:20])[NH2:35]

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 22480346HCID 22480346, compound

Product 1

HCID 22479683HCID 22479683, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A sealed tube containing tert-butyl 3-{[1-acetyl-3-(4-fluorophenyl)-1H-indazol-5-yl]carbonylamino}propanoate (115 mg, 0.270 mmol) and methanol saturated with ammonium hydroxide (2 mL) was heated to 80° C. for 18 hours. The solution was condensed to give an oil. The oil was dissolved in dimethyl formamide (5 mL) with N—N′-carbonyldiimidazole (110 mg). The solution was allowed to stir for two hours at ambient temperature. Ammonium acetate (160 mg) was added and the reaction mixture was allowed to stir at ambient conditions under nitrogen for 18 hours. The mixture was condensed and extracted with 5% sodium bicarbonate and ethyl acetate. The extracts were dried over sodium sulfate, filtered and condensed to give the title compound (17 mg, 19% yield) after purification by preparative-HPLC. 1H NMR (DMSO-d6) δ 8.65 (br s, 1H), 8.47 (s, 1H), 8.00 (m, 2H), 7.84 (d, 1H), 7.59 (d, 1H), 7.43 (br, 1H), 7.35 (t, 2H), 6.84 (s, 1H), 3.45 (m, 2H), 2.39 (m, 2H); ES-MS (m/z) 327[M+1]+.

Workup

  1. customcondensed
  2. customto give an oil
  3. stirringto stir at ambient conditions under nitrogen for 18 hours
  4. customcondensed
  5. extractionextracted with 5% sodium bicarbonate and ethyl acetate
  6. dry with materialThe extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customcondensed

Sources & evidence

ORD record
ord-067b962528664f67be7ba0878d300a77
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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