Diisopropylamine → HCID 67091398, compound

HRID 2075723Notes

Reaction equation

HRID 2075723 reaction equation
N(C(C)C)C(C)C.C([Li])CCC.[C:13]1([C:19]2[N:23]3[C:24]4[C:29]([CH:30]=[CH:31][C:22]3=[N:21][N:20]=2)=[CH:28][C:27]([S:32][C:33]2[S:34][CH:35]=[CH:36][N:37]=2)=[CH:26][CH:25]=4)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:38]1([C:41]([CH:43]2[CH2:45][CH2:44]2)=[O:42])[CH2:40][CH2:39]1>C1COCC1>[CH:38]1([C:41]([CH:43]2[CH2:45][CH2:44]2)([C:35]2[S:34][C:33]([S:32][C:27]3[CH:28]=[C:29]4[C:24](=[CH:25][CH:26]=3)[N:23]3[C:19]([C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)=[N:20][N:21]=[C:22]3[CH:31]=[CH:30]4)=[N:37][CH:36]=2)[OH:42])[CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 70721Dicyclopropyl ketoneHCID 58257814HCID 58257814, compoundHCID 178418339Butyllithium

Product 1

HCID 67091398HCID 67091398, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

iPr2NH (0.12 g, 0.84 mmol) was dissolved in THF (2 mL) and cooled to −78° C. n-Butyllithium (2.5M, 0.37 mL, 0.84 mmol) was added dropwise, followed by 10f (150 mg, 0.42 mmol) in THF (5 mL). Dicyclopropylmethanone (53 mg, 0.46 mmol) in THF (0.25 mL) was added, and the reaction was stirred overnight at room temperature. The reaction was quenched with 5% aqueous NH4Cl (10 mL). The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by preparative HPLC to give the desired product, 10g.

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched with 5% aqueous NH4Cl (10 mL)
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cbb8e874d17146dfb86e93728925b1b2
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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