Triethylamine → HCID 86677354, compound

HRID 873428Notes

Reaction equation

HRID 873428 reaction equation
[NH2:1][CH2:2][C:3]1[C:4](=[O:14])[NH:5][C:6]([CH:10]2[CH2:13][CH2:12][CH2:11]2)=[CH:7][C:8]=1[CH3:9].[NH2:15][CH2:16][C:17]1[C:18](=[O:28])[NH:19][C:20]([CH3:27])=[CH:21][C:22]=1[CH:23]1[CH2:26][CH2:25][CH2:24]1.CC([O:33][C:34](OC(OC(C)(C)C)=O)=[O:35])(C)C.C(N(CC)CC)C>C1COCC1.CN(C=O)C>[CH3:26][C:23]([N:1]([CH2:2][C:3]1[C:4](=[O:14])[NH:5][C:6]([CH:10]2[CH2:11][CH2:12][CH2:13]2)=[CH:7][C:8]=1[CH3:9])[C:34](=[O:33])[O-:35])([CH3:22])[CH3:24].[CH3:13][C:10]([N:15]([CH2:16][C:17]1[C:18](=[O:28])[NH:19][C:20]([CH3:27])=[CH:21][C:22]=1[CH:23]1[CH2:26][CH2:25][CH2:24]1)[C:34](=[O:33])[O-:35])([CH3:6])[CH3:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 67464880HCID 67464880, compoundHCID 674669403-(aminomethyl)-4-cyclobutyl-6-methyl-2(1H)-pyridinone

Product 2

HCID 86677354HCID 86677354, compoundYield 20%HCID 866773551,1-Dimethylethyl[(4-cyclobutyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamateYield 9.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

To an ice bath cooled solution of 3-(aminomethyl)-6-cyclobutyl-4-methyl-2(1H)-pyridinone and 3-(aminomethyl)-4-cyclobutyl-6-methyl-2(1H)-pyridinone (3.5 g, 18 mmol) in THF (10 mL) and DMF (10 mL) were added Boc2O (4.68 g, 21.8 mmol) and triethylamine (5.4 g, 54 mmol). The contents were then stirred for 30 min. at 30° C. The reaction was quenched by addition of ice water, during which time precipitation occurred. The reaction mixture was filtered and dried to give a mixture of the crude products. The crude products were separated by HPLC to give 1,1-dimethylethyl[(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate (2.1 g, 20%) and 1,1-dimethylethyl[(4-cyclobutyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate (1 g, 9.5%). Data for 1,1-dimethylethyl[(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate: 1H NMR (400 MHz, DMSO-d6) δ 11.28 (br s, 1H), 6.49 (br s, 1H), 5.86 (br s, 1H), 3.85 (br s, 2H), 1.97-2.14 (m, 7H), 1.87-1.94 (m, 1H), 1.72-1.77 (m, 1H), 1.28 (s, 9H).

Workup

  1. customThe reaction was quenched by addition of ice water, during which time precipitation
  2. filtrationThe reaction mixture was filtered
  3. customdried
  4. customto give
  5. customThe crude products were separated by HPLC

Sources & evidence

ORD record
ord-52f2f0c8f2e042fc80ecc4725fcd3244
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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