Ethyl Acetate → HCID 178523570, compound

HRID 722263Notes

Reaction equation

HRID 722263 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH:14]1[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]1[NH:23][CH2:24][C:25]#[N:26])=[O:12])=[CH:5]2.[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+].CCOC(C)=O>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@@H:14]1[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]1[NH:23][CH2:24][C:25]1[NH:29][N:28]=[N:27][N:26]=1)=[O:12])=[CH:5]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21883935HCID 21883935, compound

Product 1

HCID 178523570HCID 178523570, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

5-Chloro-N-{1-[(cyanomethyl)amino]-2,3-dihydro-1H-inden-2-yl}-1H-indole-2-carboxamide (Example 25; 182 mg, 0.5 mmol), sodium azide (195 mg, 3.0 mmol) and ammonium chloride (163 mg, 3.05 mmol) in DMA (5 mL) were heated in a microwave at 180° C. for 1 min. EtOAc (50 mL) was added and the mixture washed with water (6×10 mL), brine (25 mL), dried (MgSO4) and the volatiles removed by evaporation under reduced pressure. The desired component was isolated by preparative HPLC (CH3CN:water) to give the title compound (35 mg, 14%) as a pale orange powder.

Workup

  1. washthe mixture washed with water (6×10 mL), brine (25 mL)
  2. dry with materialdried (MgSO4)
  3. customthe volatiles removed by evaporation under reduced pressure
  4. customThe desired component was isolated by preparative HPLC (CH3CN:water)

Sources & evidence

ORD record
ord-1e1ff84c4dc94d21a8c0847c3a577a6c
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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