Water → HCID 86684392, compound

HRID 1411824Notes

Reaction equation

HRID 1411824 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:19][CH2:18][N:17]3[C:10](=[CH:11][C:12]4[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]=43)[C:9]2=[O:22])[C:3]=1[CH:23]=[O:24].CC(=CC)C.[O-:30]Cl=O.[Na+].O>ClCCl.C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:19][CH2:18][N:17]3[C:10](=[CH:11][C:12]4[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]=43)[C:9]2=[O:22])[C:3]=1[C:23]([OH:30])=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 768540784-chloro-2-(7,7-dimethyl-1-oxo-1,3,4,6,7,8-hexahydro-2H-cyclopenta(4,5)pyrrolo(1,2-a)pyrazin-2-yl)nicotinaldehyde

Product 1

HCID 86684392HCID 86684392, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
-10 °C

Procedure

To a mixture of 4-chloro-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridine-3-carbaldehyde 108a (500 mg, 1.46 mmol), tert-butyl alcohol (20 mL), and dichloromethane (5 mL) was added 2-methyl-2-butene (3066 mg, 43.8 mmol). An aqueous solution (8 mL) of NaClO2 (263 mg, 2.92 mmol) and NaH2PO4.2 water (683 mg, 4.38 mmol) was added dropwise at −10° C. and the reaction mixture was stirred at −10° C. for overnight. It was concentrated under reduced pressure and the residue was extracted with ethyl acetate (4×20 mL). The combined organic extract was dried over MgSO4 and concentrated. The residue was purified with reverse-phase prep-HPLC to afford 210a (315 mg, 60%) as a pale yellow solid. MS-ESI: [M+H]+ 360.1

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate (4×20 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-5742c784a8d0434ca5c38b141770daee
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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