Ammonia → HCID 9856583, compound

HRID 1765569Notes

Reaction equation

HRID 1765569 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-ec8c735bd0b7489aad2c513969527512
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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