Triethylamine → HCID 10026902, compound

HRID 1984245Notes

Reaction equation

HRID 1984245 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][NH:4][C:5]1[C:10]([C:11]#[C:12][CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:9][N:8]=[C:7]([C:20]#[N:21])[N:6]=1.[Cl:24][CH2:25][CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29].C(N(CC)CC)C.[Cl-].[NH4+]>C(Cl)Cl>[Cl:24][CH2:25][CH2:26][CH2:27][S:28]([N:17]1[CH2:18][CH2:19][N:14]([CH2:13][C:12]#[C:11][C:10]2[C:5]([NH:4][CH2:3][C:2]([CH3:23])([CH3:22])[CH3:1])=[N:6][C:7]([C:20]#[N:21])=[N:8][CH:9]=2)[CH2:15][CH2:16]1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 25517Ammonium ChlorideHCID 57714111HCID 57714111, compound

Product 1

HCID 10026902HCID 10026902, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2,2-dimethyl-propylamino)-5-(3-piperazin-1-yl-prop-1-ynyl)-pyrimidine-2-carbonitrile (0.16 mmol) in CH2Cl2 (5 ml), 3-chloropropanesulfonyl chloride (0.192 mmol) and triethylamine (0.192 mmol) are added at 0° C. The reaction mixture is stirred at room temperature for 14 h and then saturated aqueous solution of ammonium chloride is added to the reaction mixture. The mixture is extracted with two 50 ml portions of AcOEt. The combined extracts are washed with brine, dried over sodium sulfate and concentrated under vacuum. The purification of the residue by silica gel column chromatography affords 37 mg of title compound in 51% yield. Rf=0.33(AcOEt only)

Workup

  1. extractionThe mixture is extracted with two 50 ml portions of AcOEt
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe purification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-f32ba86c0013447897fb1b0103b297ee
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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