Dichloromethane → HCID 59311568, compound

HRID 1693269Notes

Reaction equation

HRID 1693269 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][C:13]1[N:18]=[C:17]([N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:16]=[C:15]2[N:34]([CH2:42][C:43]3[C:48]([CH3:49])=[C:47]([O:50][CH3:51])[C:46]([CH3:52])=[CH:45][N:44]=3)[N:35]=[C:36]([CH2:37][CH:38]([C:40]#[N:41])[OH:39])[C:14]=12.ClCCl.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:39][CH:38]([C:40]#[N:41])[CH2:37][C:36]2[C:14]3[C:15](=[N:16][C:17]([N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[N:18][C:13]=3[Cl:12])[N:34]([CH2:42][C:43]3[C:48]([CH3:49])=[C:47]([O:50][CH3:51])[C:46]([CH3:52])=[CH:45][N:44]=3)[N:35]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 59311439HCID 59311439, compound

Product 1

HCID 59311568HCID 59311568, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

p-Toluenesulfonyl chloride (511 mg) was added to a mixture composed of the above crude di-tert-butyl {4-chloro-3-(2-cyano-2-hydroxyethyl)-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate (788 mg) and dehydrated dichloromethane (12 mL), followed by dropwise addition of triethylamine (0.56 mL). Then, 4-dimethylaminopyridine (16 mg) was added and the mixture was stirred at room temperature for three hours. The reaction mixture was diluted with chloroform and washed with water. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (450 mg, 45%) as a solid.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-22b9e0ced9684befb85b43a0337405c1
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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