Sodium Hydroxide → HCID 131732099, compound

HRID 341223Notes

Reaction equation

HRID 341223 reaction equation
C[N:2](C)/[CH:3]=[N:4]/[C:5]([C:7]1[CH:12]=[CH:11][N:10]2[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[O:24])[CH:17]=3)=[CH:14][N:15]=[C:9]2[CH:8]=1)=[O:6].[OH-:32].[Na+].[CH3:34][C:35](O)=O.O>>[CH3:14][CH2:13][CH:16]([CH2:17][CH2:18][C:19]([OH:32])([CH2:35][CH3:34])[CH3:20])[CH3:21].[O:6]1[C:5]([C:7]2[CH:12]=[CH:11][N:10]3[C:13]([C:16]4[CH:17]=[C:18]([NH:22][C:23]([NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[O:24])[CH:19]=[CH:20][CH:21]=4)=[CH:14][N:15]=[C:9]3[CH:8]=2)=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21899381Acetic acid--water (1/1)HCID 178484336HCID 178484336, compound

Product 1

HCID 131732099HCID 131732099, compound

Procedure

Hydroxylamine. HCl (30 mg, 0.43 mmol) was added to 3-{3-[3-(2,2,2-trifluoro-ethyl)-ureido]-phenyl}-imidazo[1,2-a]pyridine-7-carboxylic acid 1-dimethylamino-meth-(E)-ylideneamide (135 mg, 0.3 mmol) and 5N NaOH (75 μl, 0.38 mmol) in AcOH/H2O (7:3, 1 ml) at RT. The reaction mixture was stirred at room temperature for 2 h before being heated at 60° C. for 7 h. The reaction mixture was allowed to cool then the volatiles removed in vacuo. The residue was purified by preparative HPLC to afford the desired product (35 mg). MS: [M+H]+ 403.

Workup

  1. temperaturebefore being heated at 60° C. for 7 h
  2. temperatureto cool
  3. customthe volatiles removed in vacuo
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4c47915b339b4fc691d3070aa5d6e469
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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