Pyridine → HCID 67195545, compound

HRID 550804Notes

Reaction equation

HRID 550804 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:20]3[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]3)[C:12]3[CH2:17][S:16](=[O:19])(=[O:18])[CH2:15][C:13]=3[N:14]=2)=[C:4]([F:27])[CH:3]=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:30].N1C=CC=CC=1.[Cl-].[NH4+]>C(Cl)Cl>[C:29](=[O:30])([O:31][C:32]1[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=1)[O:26][CH:23]1[CH2:24][CH2:25][N:20]([C:11]2[C:12]3[CH2:17][S:16](=[O:18])(=[O:19])[CH2:15][C:13]=3[N:14]=[C:9]([C:5]3[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[CH:3][C:4]=3[F:27])[N:10]=2)[CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 821294-Nitrophenyl chloroformateHCID 67199175HCID 67199175, compound

Product 1

HCID 67195545HCID 67195545, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 571 mg of 1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-ol, 0.30 g of 4-nitrophenyl chloroformate, 0.12 ml of pyridine, and 10 ml of methylene chloride was stirred at ambient temperature for 17 hours. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted twice with chloroform. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to yield 894 mg of 1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl 4-nitrophenyl carbonate as light yellow solid.

Workup

  1. extractionthe mixture was extracted twice with chloroform
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-15f4b1f63a7448899f1aa7f95a1caa04
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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