5-Nitro-2-Furoic Acid → 1-(9H-carbazol-4-yloxy)-3-{[1-(5-nitro-2-furoyl)piperidin-4-yl]amino}propan-2-ol

HRID 507339

反応式

HRID 507339 の反応式
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:33]1[C:45]2[NH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[C:36]([O:46][CH2:47][CH:48]([OH:57])[CH2:49][NH:50][CH:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)=[CH:35][CH:34]=1>CN(C=O)C.C(Cl)Cl>[CH:33]1[C:45]2[NH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[C:36]([O:46][CH2:47][CH:48]([OH:57])[CH2:49][NH:50][CH:51]2[CH2:52][CH2:53][N:54]([C:9]([C:7]3[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:11])[CH2:55][CH2:56]2)=[CH:35][CH:34]=1

参加物

7

反応物 4

HCID 125775-Nitro-2-Furoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 588781181-(9H-carbazol-4-yloxy)-3-(piperidin-4-ylamino)propan-2-ol

生成物 1

HCID 167312171-(9H-carbazol-4-yloxy)-3-{[1-(5-nitro-2-furoyl)piperidin-4-yl]amino}propan-2-ol収率 32%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-Nitrofuroic acid (0.14 g, 0.88 mmol) in DMF (6 mL) was added TEA (0.17 mL, 1.2 mmol), EDCI (0.2 g, 1.0 mmol), HOBt (0.031 g, 0.23 mmol), followed by 1-(9H-carbazol-4-yloxy)-3-(piperidin-4-ylamino)propan-2-ol (0.2 g, 0.6 mmol, prepared by following the procedure described in step 11, example 64). The reaction was stirred at room temperature for 12 hours and was diluted with DCM (25 mL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4, concentrated and purified by silica gel column chromatography using DCM/MeOH (9.5:0.5) to afford the title compound as red colored paste (45 mg, 32% yield). 1H NMR (400 MHz, DMSO): δ 1.20-1.80 (m, 3H), 1.90-2.30 (m, 2H), 2.50-3.60 (m, 6H), 4.00-4.60 (m, 3H), 6.72 (d, 1H, J=8.0 Hz), 6.90-7.60 (m, 6H), 7.77 (d, 1H, J=3.6 Hz), 8.22 (d, 1H, J=8.0 Hz), and 11.30 (s, 1H). MS m/z: 478.1 (M+).

後処理

  1. customprepared
  2. washwashed with water and brine solution
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-0eb2234be5104da5a65f085d2f234fac
出典データセット
uspto-grants-2010_08
特許番号
US07786142B2

関連ノート

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