Triethylamine → 1,1-Dimethylethyl [(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate

HRID 1616842노트

반응식

HRID 1616842 반응식
[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.[CH3:29][C:30]([O:33][C:34](O[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:35])([CH3:32])[CH3:31].C(N(CC)CC)C>C1COCC1.CN(C=O)C>[CH:10]1([C:6]2[NH:5][C:4](=[O:14])[C:3]([CH2:2][NH:1][C:34](=[O:35])[O:33][C:30]([CH3:32])([CH3:31])[CH3:29])=[C:8]([CH3:9])[CH:7]=2)[CH2:11][CH2:12][CH2:13]1.[CH:23]1([C:22]2[CH:21]=[C:20]([CH3:27])[NH:19][C:18](=[O:28])[C:17]=2[CH2:16][NH:15][C:37](=[O:38])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43])[CH2:24][CH2:25][CH2:26]1

참가 물질

8

반응물 4

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

생성물 2

HCID 679517401,1-Dimethylethyl [(4-cyclobutyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate수율 9.5%HCID 679517421,1-Dimethylethyl [(6-cyclobutyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]carbamate수율 20%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
30 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-857fc5cb9ab74819b9fff43b2c8a1053
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765792B2

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