Pyrrolidine → HCID 68425711, compound

HRID 1818928Notes

Reaction equation

HRID 1818928 reaction equation
O[CH2:2][CH2:3][C:4]#[C:5][C:6]1[S:14][C:13]2[C:12]([NH:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:36])[C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=4)=[CH:20][CH:19]=3)=[N:11][CH:10]=[N:9][C:8]=2[CH:7]=1.CS(Cl)(=O)=O.[NH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1>ClCCl>[N:42]1([CH2:2][CH2:3][C:4]#[C:5][C:6]2[S:14][C:13]3[C:12]([NH:15][CH2:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:36])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=5)=[CH:20][CH:19]=4)=[N:11][CH:10]=[N:9][C:8]=3[CH:7]=2)[CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 68425529HCID 68425529, compound

Product 1

HCID 68425711HCID 68425711, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 23.1 (0.27 mmol) in dichloromethane was added sequentially TEA (3.0 equiv.) and methanesulfonyl chloride (2.5 equivalents). After stirring at room temperature for 2 hours, excess pyrrolidine (−5.0 equivalent) was added and the reaction was heated at 40° C. until starting material is consumed. The reaction was cooled, concentrated to dryness and purified by flash column chromatography on silica gel to provide N-(4-{2-[6-(4-pyrrolidin-1-yl-but-1-ynyl)-thieno[3,2-d]pyrimidin-4-ylamino]-ethyl}-phenyl)-3-trifluoromethyl-benzamide (compound 23.2).

Workup

  1. temperaturethe reaction was heated at 40° C.
  2. customis consumed
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated to dryness
  5. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-22bfea0cdd1a4263b83db1196c702cca
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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