Triethylamine → HCID 86677354, 화합물

HRID 1477012노트

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HRID 1477012 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.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]

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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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-9686d6197d434da0b436a051337457d6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09402836B2

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