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

HRID 593856ノート

反応式

HRID 593856 の反応式
[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

参加物

8

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
30 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a26589d79b294e8f8d655877361e3072
出典データセット
uspto-grants-2016_01
特許番号
US09242962B2

反応ノート

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