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Methylamine → (racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-(1-(methylamino)ethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1777992
ノート
印刷プレビュー

反応式

HRID 1777992 の反応式
CS(O[CH:6]([C:8]1[C:9]([CH:34]([O:37][CH3:38])[O:35][CH3:36])=[N:10][C:11]2[N:12]([C:18](=[O:33])[NH:19][C:20]3[CH:25]=[C:24]([NH:26][CH2:27][CH2:28][O:29][CH3:30])[C:23]([C:31]#[N:32])=[CH:22][N:21]=3)[CH2:13][CH2:14][CH2:15][C:16]=2[CH:17]=1)[CH3:7])(=O)=O.[CH3:39][NH2:40]>C(Cl)Cl.CN(C=O)C.O>[C:31]([C:23]1[C:24]([NH:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:25][C:20]([NH:19][C:18]([N:12]2[C:11]3[C:16](=[CH:17][C:8]([CH:6]([NH:40][CH3:39])[CH3:7])=[C:9]([CH:34]([O:37][CH3:38])[O:35][CH3:36])[N:10]=3)[CH2:15][CH2:14][CH2:13]2)=[O:33])=[N:21][CH:22]=1)#[N:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6329MethylamineHCID 118036849(Racemic) 1-(8-((5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethyl methanesulfonate2 回

生成物 1

HCID 118036356(racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-(1-(methylamino)ethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of (racemic) 1-(8-((5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethyl methanesulfonate (intermediate 182, 231 mg, 0.421 mmol) in DCM (8 ml) and DMF (0.5 ml) at 0° C. was added methylamine (2M in THF, 3 mL, 6.00 mmol). The reaction mixture was allowed to warm to room temperature and continued to stir over night. The reaction mixture was diluted with water and DCM, phases were separated and the water phase was extracted with DCM (3×), organic phases were combined, dried using Na2SO4, filtered and concentrated. The crude product was purified using silica gel column chromatography eluting with MeOH (including 3% NH3, 4-5%) in DCM to yield the title compound as a colorless solid. (UPLC-MS 3) tR 0.76 min, ESI-MS 484.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 13.70 (s, 1H), 8.18 (s, 1H), 8.09 (s, 1H), 7.55 (s, 1H), 5.42 (s, 1H), 5.25 (t, 1H), 4.80-4.70 (m, 1H), 4.11-3.93 (m, 2H), 3.62 (t, 2H), 3.52-3.42 (m, 8H), 3.39 (s, 3H), 2.99-2.81 (m, 2H), 2.38 (s, 3H), 2.05-1.93 (m, 2H), 1.54 (d, J=6.6 Hz, 3H), 1.24 (s, 1H).

後処理

  1. customwere separated
  2. extractionthe water phase was extracted with DCM (3×), organic phases
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified
  7. washeluting with MeOH (including 3% NH3, 4-5%) in DCM

出典と根拠

ORDレコード
ord-16dd6213d75b46b281cb5f4cac3b1daf
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266883B2

反応ノート

読み込み中…

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