Dichloromethane → HCID 86641324, compound

HRID 1693287Notes

Reaction equation

HRID 1693287 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]1[C:16]2[CH2:15][S:14][N:13]=[C:12]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]3=[N:32][N:33]([CH2:35][C:36]4[C:41]([CH3:42])=[C:40]([O:43][CH3:44])[C:39]([CH3:45])=[CH:38][N:37]=4)[N:34]=[C:9]([C:10]=23)[CH2:8]1.ClCCl>C(N(CC)CC)C>[CH3:1][S:2]([O:6][CH:7]1[C:16]2[CH2:15][S:14][N:13]=[C:12]([N:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:11]3=[N:32][N:33]([CH2:35][C:36]4[C:41]([CH3:42])=[C:40]([O:43][CH3:44])[C:39]([CH3:45])=[CH:38][N:37]=4)[N:34]=[C:9]([C:10]=23)[CH2:8]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 86641323HCID 86641323, compound

Product 1

HCID 86641324HCID 86641324, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Methanesulfonyl chloride (39 μL) was added dropwise to a mixture composed of di-tert-butyl {8-hydroxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 32 (240 mg), dehydrated dichloromethane (6 mL) and triethylamine (88 μL) under cooling in an ice bath. The ice bath was removed and the mixture was stirred for two hours. After confirming that the raw material disappeared, 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. Dichloromethane and hexane were added to the residue, and the precipitated solid was collected by filtration to obtain the title compound (253 mg, 93%). The resulting compound was directly used for the next reaction without purification.

Workup

  1. temperatureunder cooling in an ice bath
  2. customThe ice bath was removed
  3. additionthe reaction mixture was diluted with chloroform
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionDichloromethane and hexane were added to the residue
  9. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-6a57a17b3f72438689d53d65acbfe12b
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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