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1,1'-Carbonyldiimidazole → (R)-N-(1-(3,4-dichlorophenyl)ethyl)-2-(2-ethoxypyridin-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

HRID 2279497
ノート
印刷プレビュー

反応式

HRID 2279497 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH2:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.[CH2:24]([O:26][C:27]1[CH:32]=[C:31]([NH:33][C:34]2[N:35]=[CH:36][C:37]3[CH2:43][CH2:42][NH:41][CH2:40][C:38]=3[N:39]=2)[CH:30]=[CH:29][N:28]=1)[CH3:25].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:11][C:17]([N:41]2[CH2:42][CH2:43][C:37]3[CH:36]=[N:35][C:34]([NH:33][C:31]4[CH:30]=[CH:29][N:28]=[C:27]([O:26][CH2:24][CH3:25])[CH:32]=4)=[N:39][C:38]=3[CH2:40]2)=[O:18])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]
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 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 793515(R)-1-(3,4-dichlorophenyl)ethanamineHCID 68294219N-(2-ethoxypyridin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine

生成物 1

HCID 60198529(R)-N-(1-(3,4-dichlorophenyl)ethyl)-2-(2-ethoxypyridin-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

実験手順

A vial was charged with 185 (0.105 g, 0.553 mmol), CDI (0.0896 g, 0.553 mmol) and DCM (2 mL) and stirred for 30 min. To the solution was added 186 (0.150 g, 0.553 mmol) and DIPEA (0.193 ml, 1.11 mmol) and the resulting reaction stirred for 3 d. The reaction was washed with brine (4 mL), and the organic phase concentrated and loaded on to a preparative SiO2 plate (1.0 mm thickness) which was developed with EtOAc/MeOH (95:5) and eluted to afford 0.038 g (13%) of I-35: 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.96 (d, 1H), 7.73 (s, 1H), 7.44 (m, 1H), 7.35 (d, 1H), 7.29 (m, 1H), 7.20 (m, 1H), 6.95 (m, 1H), 5.40 (d, 1H), 5.00 (m, 1H), 4.49 (s, 1H), 4.36 (q, 2H), 3.68 (m, 2H), 2.72 (d, 2h), 1.49 (d, 3H), 1.39 (t, 3H); m/z (APCI-pos) M+1=487.2.

後処理

  1. customthe resulting reaction
  2. stirringstirred for 3 d
  3. washThe reaction was washed with brine (4 mL)
  4. concentrationthe organic phase concentrated
  5. washeluted
  6. customto afford 0.038 g (13%) of I-35: 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.96 (d, 1H), 7.73 (s, 1H), 7.44 (m, 1H), 7.35 (d, 1H), 7.29 (m, 1H), 7.20 (m, 1H), 6.95 (m, 1H), 5.40 (d, 1H), 5.00 (m, 1H), 4.49 (s, 1H), 4.36 (q, 2H), 3.68 (m, 2H), 2.72 (d, 2h), 1.49 (d, 3H), 1.39 (t, 3H)

出典と根拠

ORDレコード
ord-02e1721bff334693b486ee6ffa3edb30
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133187B2

反応ノート

読み込み中…

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