Diisopropylethylamine → HCID 73438418, compound

HRID 1777286Notes

Reaction equation

HRID 1777286 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]1)[CH2:10]2)=[O:5])[CH3:2].Cl.[CH3:24][C:25]1([NH2:29])[CH2:28][CH2:27][CH2:26]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:24][C:25]1([NH:29][C:20]([CH:17]2[CH2:18][CH2:19][N:14]([CH:9]3[CH2:10][CH:11]4[N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]([CH2:13][CH2:12]4)[CH2:8]3)[CH2:15][CH2:16]2)=[O:22])[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 183324491-Methylcyclobutan-1-amine hydrochlorideHCID 90079654HCID 90079654, compound

Product 1

HCID 73438418HCID 73438418, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[8-(Ethoxycarbonyl)-8-azabicyclo[3.2.1]oct-3-yl]piperidine-4-carboxylic acid (0.50 g assumed 1.62 mmol) was dissolved in DMF (8 mL) and (1-methylcyclobutyl)amine hydrochloride (0.295 g, 2.44 mmol), HATU (0.926 g, 2.44 mmol) and DIPEA (1.05 g, 1.41 mL, 8.12 mmol) were added. The reaction mixture was stirred at rt for 60 h and the solvents were removed in vacuo. The residue was partitioned between DCM and sat. NaHCO3 sol., the organic layer was washed with sat. NaCl sol. and passed through a phase separator cartridge. The solvents of the organic filtrate were removed in vacuo, and the residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 25 g, 40-6 3 μm, 60 A, 25 mL per min, gradient 0% to 10% MeOH in DCM]) to give ethyl 3-{4-[(1-methylcyclobutyl)carbamoyl]piperidin-1-yl}-8-azabicyclo[3.2.1]octane-8-carboxylate isomer 1 (0.208 g, 34%) as a light yellow gum.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was partitioned between DCM and sat. NaHCO3 sol.
  3. washthe organic layer was washed with sat. NaCl sol.
  4. customThe solvents of the organic filtrate were removed in vacuo
  5. customthe residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 25 g, 40-6 3 μm, 60 A, 25 mL per min, gradient 0% to 10% MeOH in DCM])

Sources & evidence

ORD record
ord-e56e3bd391ea41f893770c90fe0df4f5
Source dataset
uspto-grants-2016_02
Patent number
US09266857B2

Reaction notes

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