Ammonia → HCID 21054821, compound

HRID 2215575Notes

Reaction equation

HRID 2215575 reaction equation
[CH3:1][N:2]([C:15]1[CH:20]=[C:19]([O:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27]([C:31](=[O:34])[NH:32][CH3:33])[CH:26]=[CH:25]3)[CH:18]=[CH:17][N:16]=1)[C:3](=O)[O:4]C1C=CC([N+]([O-])=O)=CC=1.[NH3:35]>CN(C)C=O>[CH3:33][NH:32][C:31]([N:27]1[C:28]2[C:24](=[CH:23][C:22]([O:21][C:19]3[CH:18]=[CH:17][N:16]=[C:15]([N:2]([CH3:1])[C:3]([NH2:35])=[O:4])[CH:20]=3)=[CH:30][CH:29]=2)[CH:25]=[CH:26]1)=[O:34]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21949228HCID 21949228, compound

Product 1

HCID 21054821HCID 21054821, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitrophenyl N-methyl-(4-(1-methylcarbamoyl-indol-5-yloxy)pyridin-2-yl)carbamate (105 mg, 0.228 mmol) was dissolved in N,N-dimethylformamide (2.5 ml); aqueous ammonia (0.5 ml, 28.0%) was added thereto; the reaction mixture was stirred at room temperature for 10.5 hours. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained crystals were suspended in ethanol: diethyl ether=1:1 (6 ml), filtered off, washed with diethyl ether, and dried to yield the title compound (37 mg, 0.11 mmol, 48%) as pale yellow crystals.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washand the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationdiethyl ether=1:1 (6 ml), filtered off
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-436e95e2f16d464a8954561b249f2271
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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