Ammonia → HCID 44609420, compound

HRID 2094203Notes

Reaction equation

HRID 2094203 reaction equation
ClC(Cl)(Cl)[C:3]([N:5]=C=O)=[O:4].[NH2:10][C:11]1[NH:12][C:13]2[C:18]([C:19]=1[C:20]([NH2:22])=[O:21])=[CH:17][CH:16]=[C:15]([O:23][CH3:24])[CH:14]=2.N.CO>O1CCCC1>[NH2:5][C:3]([NH:10][C:11]1[NH:12][C:13]2[C:18]([C:19]=1[C:20]([NH2:22])=[O:21])=[CH:17][CH:16]=[C:15]([O:23][CH3:24])[CH:14]=2)=[O:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 76400Trichloroacetyl isocyanateHCID 58280308HCID 58280308, compound

Product 1

HCID 44609420HCID 44609420, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trichloroacetyl isocyanate (1.7 mL, 14 mmol) was added dropwide to a solution of 2-amino-6-methoxyindole-3-carboxamide (Reference compound No.2-1, 2.9 g, 14 mmol) in anhydrous tetrahydrofuran (50 mL) at −40° C. over a period of 10 minutes and the mixture was stirred for 2.5 hours. Moreover, 2.0 M ammonia in methanol solution (40 mL, 80 mmol) was added thereto and the mixture was stirred overnight at room temperature. The reaction solution was concentrated in vacuo, and the obtained solid was filtered off and washed with a mixed solvent of chloroform-methanol (50 mL). The solid was dried at 40° C. under reduced pressure to give the title compound (3.1 g) as a gray solid (88%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. concentrationThe reaction solution was concentrated in vacuo
  3. filtrationthe obtained solid was filtered off
  4. washwashed with a mixed solvent of chloroform-methanol (50 mL)
  5. customThe solid was dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-434ef7e15e35440eb76fadbba8ea8a6a
Source dataset
uspto-grants-2013_05
Patent number
US08445529B2

Reaction notes

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