Acetate → HCID 68096439, compound

HRID 1918939Notes

Reaction equation

HRID 1918939 reaction equation
[N:1]1[N:9]2[C:4]([CH2:5][O:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[NH:10][C:11]1[C:12](=[O:27])[N:13]([CH3:26])[CH:14]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:16]=1.[C:28]([O:31][CH2:32][C:33]1[C:38]([N:39]2[CH2:50][CH2:49][N:48]3[C:41](=[CH:42][C:43]4[CH2:44][C:45]([CH3:52])([CH3:51])[CH2:46][C:47]=43)[C:40]2=[O:53])=[CH:37][CH:36]=[CH:35][C:34]=1Br)(=[O:30])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.C(OCC)C.O.COCCOC>[C:28]([O:31][CH2:32][C:33]1[C:34]([C:15]2[CH:16]=[C:11]([NH:10][C:2]3[CH:3]=[C:4]4[N:9]([N:1]=3)[CH2:8][CH2:7][O:6][CH2:5]4)[C:12](=[O:27])[N:13]([CH3:26])[CH:14]=2)=[CH:35][CH:36]=[CH:37][C:38]=1[N:39]1[CH2:50][CH2:49][N:48]2[C:41](=[CH:42][C:43]3[CH2:44][C:45]([CH3:52])([CH3:51])[CH2:46][C:47]=32)[C:40]1=[O:53])(=[O:30])[CH3:29]

Participants

10

Reactant 4

HCID 175AcetateHCID 10340Sodium CarbonateHCID 580440283-(6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 680968852-Bromo-6-[7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl]benzyl Acetate

Product 1

HCID 68096439HCID 68096439, compoundYield 78.2%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

A microwave tube equipped with a magnetic stirrer was charged with 175a (120 mg, 0.31 mmol), 167f (130 mg, 0.3 mmol), 1,2-dimethoxyethane (4 mL) and 1M aqueous sodium carbonate (1 mL). After bubbling N2 for 15 min, Pd(PPh3)4 (18 mg, 0.02 mmol) was added. The mixture was heated in microwave to 130° C. for 10 min. After this time, 1 acetate (5 mL) and water (5 mL) were added. The separated aqueous layer was extracted with 1 acetate (2×5 mL). The combined organics were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography eluting with a gradient of CH2Cl2-60:35:5 CH2Cl2:diethyl ether:methanol to afford a 74% yield (140 mg) of 175b

Workup

  1. customA microwave tube equipped with a magnetic stirrer
  2. customAfter bubbling N2 for 15 min
  3. extractionThe separated aqueous layer was extracted with 1 acetate (2×5 mL)
  4. washThe combined organics were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography
  9. washeluting with a gradient of CH2Cl2-60:35:5 CH2Cl2

Sources & evidence

ORD record
ord-3be8c8404b574380abdb001c32d4d86a
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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