Triethylamine → HCID 178483327, compound

HRID 1353823Notes

Reaction equation

HRID 1353823 reaction equation
Cl.C(O[CH:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[NH2:6])C.[NH2:23][NH:24][C:25](=O)[CH2:26][N:27]([CH3:29])[CH3:28].C(N(CC)CC)C>C(O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]4[NH:6][C:25]([CH2:26][N:27]([CH3:29])[CH3:28])=[N:24][N:23]=4)[CH:8]=3)[NH:12][N:11]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 683192-(Dimethylamino)acetohydrazideHCID 21101187ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methaneamine hydrochloride

Product 1

HCID 178483327HCID 178483327, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methaneamine hydrochloride (200 mg, 0.62 mmol), N-amino-2-(dimethylamino)acetamide (147.5 mg, 0.95 mmol), and molecular sieves in ethanol was added triethylamine (0.25 mL, 1.86 mmol). The reaction was allowed to stir under a nitrogen atmosphere at 75° C. overnight. The reaction was filtered using a fritted funnel and the filtrate was concentrated. This was purified by semi-preprative HPLC. The material was taken up in ethyl acetate and washed with aqueous sodium bicarbonate. This organic layer was dried with magnesium sulfate, filtered and concentrated to yield the title compound (192 mg, 23% yield). 1H NMR (CD3OD) δ 8.7 (s, 1H), 8.0–8.1 (m, 3H), 7.7 (d, 1H), 7.25 (t, 2H), 4.5 (s, 2H), 3.0 (s, 6H), ES-MS (m/z) 337 [M+1]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated
  3. customThis was purified by semi-preprative HPLC
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialThis organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-de43b2037a134752a379de3d630bd644
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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