Hydrazine hydrate (1:1) → HCID 178523378, compound

HRID 341195Notes

Reaction equation

HRID 341195 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.O.[NH2:33]N>C(O)(=O)C>[N:2]1[N:33]=[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)[NH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178484336HCID 178484336, compound

Product 1

HCID 178523378HCID 178523378, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 3-{3-[3-(2,2,2-Trifluoro-ethyl)-ureido]-phenyl}-imidazo[1,2-a]pyridine-7-carboxylic acid 1-dimethylamino-meth-(E)-ylideneamide (17 mg, 0.04 mmol) in acetic acid (0.5 ml) was added hydrazine hydrate (5 μl, 0.1 mmol). The reaction mixture was heated at 90° C. for 30 min before being cooled to room temperature. The volatiles were removed in vacuo and the residue azeotroped with toluene. Trituration of the residue with Et2O afforded a pink solid (12 mg). MS: [M+H]+ 402.

Workup

  1. temperaturebefore being cooled to room temperature
  2. customThe volatiles were removed in vacuo
  3. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-9161c24f4e424758ace2f18436736c34
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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