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Triethylamine → N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-N-cyclopropyl-3-(trifluoromethyl)benzenesulfonamide

HRID 1092553
ノート
印刷プレビュー

反応式

HRID 1092553 の反応式
[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:16][CH:17]3[CH2:19][CH2:18]3)[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:27][C:28]([F:40])([F:39])[C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1.CN(C1C=CC=CN=1)C>O1CCCC1>[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([N:16]([CH:17]3[CH2:18][CH2:19]3)[S:35]([C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:27])([F:39])[F:40])[CH:30]=3)(=[O:37])=[O:36])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 46213241(3aS*,4S*,6aR*)-2-benzyl-N-cyclopropyloctahydrocyclopenta[c]pyrrol-4-amine

生成物 1

HCID 68413617N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-N-cyclopropyl-3-(trifluoromethyl)benzenesulfonamide

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒

実験手順

(3aS*,4S*,6aR*)-2-Benzyl-N-cyclopropyloctahydrocyclopenta[c]pyrrol-4-amine (382 mg, 1.490 mmol) from Example 198, triethylamine (312 μL, 2.235 mmol), and 3-(trifluoromethyl)benzene-1-sulfonyl chloride (262 μL, 1.639 mmol) were combined in tetrahydrofuran (7 mL). A catalytic amount of (dimethylamino)pyridine was added, and the reaction mixture was stirred at room temperature overnight. The solvent was reduced in volume, and the crude material applied to silica gel and eluted with 20% to 100% ethyl acetate/hexanes to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.46 (s, 1H), 8.31 (d, J=7.9, 1H), 7.93 (d, J=7.8, 1H), 7.74 (t, J=7.9, 1H), 7.41 (d, J=7.2, 2H), 7.36 (t, J=7.4, 2H), 7.29 (t, J=7.2, 1H), 3.97 (ddd, J=6.1, 7.7, 13.5, 1H), 3.54-3.45 (m, 2H), 3.17 (dt, J=5.9, 11.8, 1H), 2.82 (dd, J=3.6, 9.7, 1H), 2.55 (t, J=8.2, 1H), 2.51-2.43 (m, 2H), 2.36-2.22 (m, 2H), 1.88-1.82 (m, 1H), 1.57 (dt, J=5.9, 11.6, 1H), 1.43-1.32 (m, 3H), 1.05-0.98 (m, 1H), 0.80 (ddd, J=6.9, 9.8, 12.4, 1H), 0.73-0.65 (m, 1H); MS (ESI+) m/z 465 (M+H)+.

後処理

  1. washeluted with 20% to 100% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-0aa60b46c25f45aaa11d58d9590301a3
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129417B2

反応ノート

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