4-Toluenesulfonyl chloride → HCID 89870710, compound

HRID 516181Notes

Reaction equation

HRID 516181 reaction equation
CCN(C(C)C)C(C)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[NH2:21][C:22]1[C:23]2[C:30]([C:31]#[C:32][C:33]3[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[C:35]([O:41][CH3:42])[CH:34]=3)=[CH:29][N:28]([C@@H:43]3[CH2:47][N:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[C@H:45]([C:55]([NH:57][NH:58][C:59](=O)[CH2:60][N:61]([CH3:63])[CH3:62])=[O:56])[CH2:44]3)[C:24]=2[N:25]=[CH:26][N:27]=1.C(OCC)(=O)C>C(#N)C.O>[NH2:21][C:22]1[C:23]2[C:30]([C:31]#[C:32][C:33]3[CH:34]=[C:35]([O:41][CH3:42])[CH:36]=[C:37]([O:39][CH3:40])[CH:38]=3)=[CH:29][N:28]([C@@H:43]3[CH2:47][N:46]([C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])[C@H:45]([C:55]4[O:56][C:59]([CH2:60][N:61]([CH3:63])[CH3:62])=[N:58][N:57]=4)[CH2:44]3)[C:24]=2[N:25]=[CH:26][N:27]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 89870921HCID 89870921, compound

Product 1

HCID 89870710HCID 89870710, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

DIPEA (105 μl) and tosyl chloride (56 mg) were added to a solution of (2S,4S)-tert-butyl 4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(2-(2-(dimethylamino)acetyl)hydrazine carbonyl)pyrrolidine-1-carboxylate (100 mg) obtained in Step 1 in acetonitrile (3 ml), and the mixture was stirred at 40° C. for 1 hour. Ethyl acetate and water were added to the reaction mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a light-yellow, amorphous substance (40.5 mg). Physical properties: m/z [M+H]+ 589.2

Workup

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol)

Sources & evidence

ORD record
ord-763cc5ba26524a21a882deb9362192a2
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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