ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Diisopropylethylamine → 1-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-N,N-dimethylpiperidine-4-sulfonamide

HRID 1619873
ノート
印刷プレビュー

反応式

HRID 1619873 の反応式
[CH3:1][N:2]([CH3:22])[S:3]([CH:6]1[CH2:11][CH2:10][N:9]([C:12](OCC2C=CC=CC=2)=O)[CH2:8][CH2:7]1)(=[O:5])=[O:4].ClC1[N:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:27]=[C:26]([N:36]2[C:40]3[CH:41]=[CH:42][CH:43]=[C:44]([O:45][CH3:46])[C:39]=3[N:38]=[C:37]2[CH:47]([F:49])[F:48])[N:25]=1.CCN(C(C)C)C(C)C>CO.C1COCC1.[Pd]>[F:49][CH:47]([F:48])[C:37]1[N:36]([C:26]2[N:27]=[C:28]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[N:29]=[C:12]([N:9]3[CH2:8][CH2:7][CH:6]([S:3]([N:2]([CH3:1])[CH3:22])(=[O:4])=[O:5])[CH2:11][CH2:10]3)[N:25]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[C:44]([O:45][CH3:46])[C:39]=2[N:38]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 534881021-[4-Chloro-6-(morpholin-4-yl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazoleHCID 53587548Benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylate

生成物 1

HCID 469175741-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-N,N-dimethylpiperidine-4-sulfonamide収率 86%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒
HCID 887Methanol溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

The above carbamate was hydrogenated over 5% Pd on carbon in MeOH. After removal of the solvent, the residue was combined with 0.19 g (0.48 mmol) 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole (Example 2) and DIPEA in THF. The mixture was heated under reflux for 30 min and the solvent was removed. After dilution with water, the resulting solid was collected and dried. Chromatography on silica, eluting with CH2Cl2/EtOAc (93:7), gave 0.227 g (86% yield) of 1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N,N-dimethyl-4-piperidinesulfonamide: mp (MeOH) 260-264° C.; 1H NMR (CDCl3) δ 7.88 (dd, J=8.4, 0.6 Hz, 1H), 7.46 (t, JHF=53.5 Hz, 1H), 7.35 (t, J=7.7 Hz, 1H), 6.81 (d, J=7.7 Hz, 1H), 4.91 (br d, J=13.5 Hz, 2H), 4.05 (s, 3H), 3.88 (m, 4H), 3.78 (m, 4H), 3.27 (tt, J=11.8, 3.8 Hz, 1H), 2.95 (s, 6H), 2.17 (dd, J=12.7, 2.2 Hz, 2H), 1.85 (dq, J=12.6, 4.2 Hz, 2H); Anal. Calcd. for C23H30F2N8O4S: C, 50.0; H, 5.5; N, 20.3. Found: C, 49.9; H, 5.5; N, 20.4%.

後処理

  1. customAfter removal of the solvent
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 min
  4. customthe solvent was removed
  5. customAfter dilution with water, the resulting solid was collected
  6. customdried
  7. washChromatography on silica, eluting with CH2Cl2/EtOAc (93:7)

出典と根拠

ORDレコード
ord-85badc7a631343e8a7e3299c868a4543
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08772287B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート