Tetrahydrofuran → HCID 58180565, compound

HRID 1188056Notes

Reaction equation

HRID 1188056 reaction equation
[CH:1]1([N:4]([CH:25]2[CH2:27][CH2:26]2)[C:5]([C:7]2[N:22]([CH2:23][CH3:24])[C:10]3=[N:11][C:12]([N:19]=[C:20]=[S:21])=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C1COCC1.[NH2:33][C:34]1[N:38]([CH3:39])[N:37]=[C:36]([CH3:40])[CH:35]=1.[H-].[Na+]>C(OCC)(=O)C>[CH:25]1([N:4]([CH:1]2[CH2:2][CH2:3]2)[C:5]([C:7]2[N:22]([CH2:23][CH3:24])[C:10]3=[N:11][C:12]([NH:19][C:20]([NH:33][C:34]4[N:38]([CH3:39])[N:37]=[C:36]([CH3:40])[CH:35]=4)=[S:21])=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 58180531Imidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide, N,N-dicyclopropyl-6-ethyl-1,6-dihydro-4-isothiocyanato-1-methyl-

Product 1

HCID 58180565HCID 58180565, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a flask charged with N,N-dicyclopropyl-6-ethyl-4-isothiocyanato-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 41A, 0.0342 g, 0.090 mmol) was added THF (0.449 mL). 5-Amino-1,3-dimethylpyrazole (0.012 g, 0.108 mmol) was added followed by sodium hydride (3.60 mg, 0.090 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate and quenched with saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate. The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude material was used without further purification.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-7598c9dfa52c4f07a0c6488c1371dc7c
Source dataset
uspto-grants-2014_03
Patent number
US08673933B2

Reaction notes

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