Ammonia → HCID 9856583, compound

HRID 549008Notes

Reaction equation

HRID 549008 reaction equation
C([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][N:26]=[C:21]3[CH:20]=2)=[CH:9]1)C1C=CC=CC=1.N.[Na].O>O1CCCC1>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH:9]=[C:10]2[C:19]1[NH:27][C:22]2=[N:23][CH:24]=[CH:25][N:26]=[C:21]2[CH:20]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 5360545SodiumHCID 9924732HCID 9924732, compound

Product 1

HCID 9856583HCID 9856583, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A cooled (−78° C.) solution of 6-(1-benzyl-5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine [50 mg, Example 1(m)] in tetrahydrofuran (20 mL) was treated with liquid ammonia (20 mL) then with sodium (100 mg). After stirring at −78° C. for 30 minutes the reaction mixture was allowed to warm slowly to ambient temperature, then treated with water (50 mL) and then extracted three times with ethyl acetate (50 mL). The combined extracts were dried over sodium sulfate and then evaporated. The residue was triturated with diethyl ether to give the title compound (14 mg) as a brown solid, m.p. 268-271° C. MS: 265.24 (MH+).

Workup

  1. temperatureto warm slowly to ambient temperature
  2. extractionextracted three times with ethyl acetate (50 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. customevaporated
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-7e55c8c0cfa74b2d98fad5f3aab7b946
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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