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Lithium Hexamethyldisilazide → HCID 86700871, compound

HRID 881762
Notes
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Reaction equation

HRID 881762 reaction equation
[Cl-].[CH3:2][O:3][CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:34]1([C:38]2[O:42][C:41]([NH:43][C:44]3[CH:45]=[CH:46][C:47]([C:50]4[CH:55]=[CH:54][C:53]([C:56]56[CH2:63][CH2:62][C:59]([CH:64]=O)([CH2:60][CH2:61]5)[CH2:58][O:57]6)=[CH:52][CH:51]=4)=[N:48][CH:49]=3)=[N:40][N:39]=2)[CH2:37][CH2:36][CH2:35]1>O1CCCC1>[CH:34]1([C:38]2[O:42][C:41]([NH:43][C:44]3[CH:49]=[N:48][C:47]([C:50]4[CH:55]=[CH:54][C:53]([C:56]56[CH2:63][CH2:62][C:59]([CH:64]=[CH:2][O:3][CH3:4])([CH2:60][CH2:61]5)[CH2:58][O:57]6)=[CH:52][CH:51]=4)=[CH:46][CH:45]=3)=[N:40][N:39]=2)[CH2:35][CH2:36][CH2:37]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 86700853HCID 86700853, compoundHCID 89872208HCID 89872208, compound

Product 1

HCID 86700871HCID 86700871, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of triphenylphosphine methoxymethane chloride (28.7 mg, 0.084 mmol) in tetahydrofuran (1 ml) was flushed with nitrogen for three times and at 0° C., and was added LiHMDS (0.079 ml, 0.084 mmol). The reddish solution was stirred at 0° C. for 30 minutes, and then at −78° C., a solution of 1-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octane-4-carbaldehyde (30 mg, 0.070 mmol) in tetrahydrofuran (0.7 ml) was added dropwise. The mixture was allowed to warm to 0° C. for 30 minutes. The reaction was quenched with water (2 ml), and the mixture was partitioned between brine (15 ml) and ethyl acetate (50 ml), aquous layer was extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine and dried over Na2SO4, and concentrated. The residue was purified by flash chromatography (heptanes/acetone 1/1) to afford 5-cyclobutyl-N-(6-(4-(4-(2-methoxyvinyl)-2-oxabicyclo[2.2.2]octan-1-yl)phenyl)pyridin-3-yl)-1,3,4-oxadiazol-2-amine (10 mg, 31%) as yellow solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.83-2.51 (m, 14H) 3.56 (s, 3H) 3.63-3.76 (m, 1H) 4.00 (d, J=6.80 Hz, 1H) 4.06 (s, 2H) 5.87 (d, J=6.80 Hz, 1H) 7.49 (d, J=8.72 Hz, 2H) 7.78-7.93 (m, 3H) 8.17 (dd, J=24.00, 8.80 Hz, 1H) 8.71 (d, J=16.80 Hz, 1H). LC/MS, [MS+1] 459.1, RT: 1.44, 1.48; (Condition E).

Workup

  1. customwas flushed with nitrogen for three times and at 0° C.
  2. temperatureto warm to 0° C. for 30 minutes
  3. customThe reaction was quenched with water (2 ml)
  4. customthe mixture was partitioned between brine (15 ml) and ethyl acetate (50 ml), aquous layer
  5. extractionwas extracted with ethyl acetate (2×50 ml)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (heptanes/acetone 1/1)

Sources & evidence

ORD record
ord-0e9595dd09ac4da6b64f857b01f5ea70
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993619B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes