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Diisopropylethylamine → O=C(Ccc(=O)OC(C)(C)C)N1ccc(=CC1)B1OC(C(O1)(C)C)(C)C

HRID 1486867
Notes
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Reaction equation

HRID 1486867 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:26][C:27]1([CH3:40])[C:31]([CH3:33])([CH3:32])[O:30][B:29]([C:34]2[CH2:35][CH2:36][NH:37][CH2:38][CH:39]=2)[O:28]1.[C:41]([O:45][C:46](=[O:52])[CH2:47][CH2:48][C:49](O)=[O:50])([CH3:44])([CH3:43])[CH3:42].C(N(CC)C(C)C)(C)C>O.CN(C=O)C>[O:50]=[C:49]([N:37]1[CH2:36][CH:35]=[C:34]([B:29]2[O:28][C:27]([CH3:40])([CH3:26])[C:31]([CH3:32])([CH3:33])[O:30]2)[CH2:39][CH2:38]1)[CH2:48][CH2:47][C:46]([O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:52]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 41391074-(Tert-butoxy)-4-oxobutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 497610841,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester hydrochloride

Product 1

HCID 131736829
O=C(Ccc(=O)OC(C)(C)C)N1ccc(=CC1)B1OC(C(O1)(C)C)(C)C
Yield 62.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (3.68 g) was added to a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (1.98 g), 4-tert-butoxy-4-oxobutanoic acid (1.686 g), N,N-diisopropylethylamine (3.38 mL), and DMF (20 mL) at 0 C, and the obtained mixture was stirred at room temperature for 3 days. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to obtain the title compound (1.84 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e788cae5e57446d086d8ea48da51673d
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428470B2

Reaction notes

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