Hydrazine hydrate (1:1) → HCID 178490275, compound

HRID 216146Notes

Reaction equation

HRID 216146 reaction equation
C[N:2](C)[C:3](=[N:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[C:17]([NH:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:16]=[C:15]([O:30][CH3:31])[N:14]=2)[CH:8]=1)[CH3:4].O.[NH2:35]N>C(O)(=O)C>[CH3:31][O:30][C:15]1[N:16]=[C:17]([NH:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH:18]=[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:6]3[NH:35][N:2]=[C:3]([CH3:4])[N:5]=3)[CH:8]=2)[N:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58990371HCID 58990371, compound2×

Product 1

HCID 178490275HCID 178490275, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(1-dimethylamino-ethylidene)-3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzamide [0.132 mmol, Intermediate (46)] and hydrazine hydrate (15 μL, 0.48 mmol) in acetic acid (1 mL) is heated to 90° C. After stirring for 30 minutes removed from heat, quenched with saturated sodium bicarbonate solution (20 mL) and extracted twice with EtOAc (20 mL). The organic extracts are dried over magnesium sulfate, filtered and concentrated by rotary evaporator. The resulting oil is subjected to flash column chromatography on silica gel eluting with 40% EtOAc in heptane gradient to afford {2-methoxy-6-[3-(5-methyl-2H-[1,2,4]triazol-3-yl)-phenyl]-pyrimidin-4-yl}-[2-(4-methoxy-phenyl)-ethyl]-amine [38 mg, 69%, Example 37]. LCMS: RT=2.59 minutes MS: 417 (M+H). IC50=3.7 nM

Workup

  1. customremoved
  2. temperaturefrom heat
  3. customquenched with saturated sodium bicarbonate solution (20 mL)
  4. extractionextracted twice with EtOAc (20 mL)
  5. dry with materialThe organic extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-1dd2fa88298e450890080808122689a1
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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