Water → HCID 10111024, compound

HRID 1835187Notes

Reaction equation

HRID 1835187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[NH:20][C:15]2=[N:16][CH:17]=[CH:18][N:19]=[C:14]2[CH:13]=1.[H-].[Na+].Cl[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:24][C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26])[CH:7]=[C:6]2[C:12]1[NH:20][C:15]2=[N:16][CH:17]=[CH:18][N:19]=[C:14]2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74040Morpholine, 4-(chloroacetyl)-HCID 9856583HCID 9856583, compound

Product 1

HCID 10111024HCID 10111024, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 6-(5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine [70 mg, Example 11] in dry dimethylformamide (10 mL) was treated with sodium hydride (21.6 mg, 60% dispersion in mineral oil). After stirring for 30 minutes this mixture was treated with a solution of 4-(2-chloroacetyl)morpholine (44.1 mg) in dimethylformamide (1 mL) and stirring was continued for a further 3 hours. The reaction mixture was poured into water (20 mL) and then extracted three times with ethyl acetate (30 mL). The combined extracts were dried over sodium sulfate and then evaporated. The residue was triturated with diethyl ether to give the title compound (55 mg) as a yellow solid, m.p. 263-267° C. MS: 392.21 (MH+).

Workup

  1. stirringstirring
  2. waitwas continued for a further 3 hours
  3. extractionextracted three times with ethyl acetate (30 mL)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customevaporated
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-5d993e503d034ebeba25c589ae5c7f0c
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

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