Dimethylamine → HCID 22730664, compound

HRID 2356013Notes

Reaction equation

HRID 2356013 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1.[C:19](Cl)(Cl)=[O:20].[CH:23]([N:26](CC)[CH:27](C)C)(C)C.CNC>ClCCl.C1(C)C=CC=CC=1.C1COCC1>[CH3:23][N:26]([CH3:27])[C:19]([NH:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1)=[O:20]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 22730091HCID 22730091, compound

Product 1

HCID 22730664HCID 22730664, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A room temperature solution of Example 43A (100 mg, 0.41 mmol) in dichloromethane (2 mL) was treated with 1.9M phosgene in toluene (0.26 mL) and N,N-diisopropylethylamine (0.2 mL, 1.2 mmol), stirred for 16 hours, treated with 2M dimethylamine in THF (0.5 mL), stirred for 1 hour, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product.

Workup

  1. stirringstirred for 1 hour
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-30e4de41c96344649310d5b673baccbf
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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