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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-[(1R,2R)-1-({[(2S)-5-oxotetrahydrofuran-2-yl]carbonyl}amino)-2,3-dihydro-1H-inden-2-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1244717
ノート
印刷プレビュー

反応式

HRID 1244717 の反応式
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[O:20]=[C:21]1[O:25][C@H:24]([C:26]([OH:28])=O)[CH2:23][CH2:22]1.CCN=C=NCCCN(C)C.[NH2:40][C@@H:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43][C@H:42]1[NH:50][C:51]([C:53]1[NH:57][C:56]2[S:58][C:59]([Cl:61])=[CH:60][C:55]=2[CH:54]=1)=[O:52]>C(Cl)Cl>[Cl:61][C:59]1[S:58][C:56]2[NH:57][C:53]([C:51]([NH:50][C@@H:42]3[CH2:43][C:44]4[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=4)[C@H:41]3[NH:40][C:26]([C@@H:24]3[CH2:23][CH2:22][C:21](=[O:20])[O:25]3)=[O:28])=[O:52])=[CH:54][C:55]=2[CH:60]=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 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 636468(2S)-5-oxooxolane-2-carboxylic acidHCID 58717470N-[(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

生成物 1

HCID 10288256
2-Chloro-N-[(1R,2R)-1-({[(2S)-5-oxotetrahydrofuran-2-yl]carbonyl}amino)-2,3-dihydro-1H-inden-2-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
収率 56%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

DIPEA (180 μL, 1.05 mmol), HOBT (68 mg, 0.5 mmol), (2S)-5-oxotetrahydrofuran-2-carboxylic acid (CAS Reg. No: [21461–84–7], 0.5 mmol, 65 mg) and EDAC (120 mg, 0.63 mmol) were added to a suspension of N-[(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 21, 223 mg, 0.5 mmol) in anhydrous DCM (7 mL). The reaction was stirred at ambient temperature for approximately 16 h. The volatiles were removed by evaporation under reduced pressure, the residue dissolved in EtOAc (5 mL), washed with water (2×5 mL), brine (10 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure and the residue triturated (EtOAc:hexane, 1:10), collected by filtration, washed with hexane (2×5 mL) and dried to give the title compound (112 mg, 56%) as a brown solid.

後処理

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (5 mL)
  3. washwashed with water (2×5 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed by evaporation under reduced pressure
  6. customthe residue triturated (EtOAc:hexane, 1:10)
  7. filtrationcollected by filtration
  8. washwashed with hexane (2×5 mL)
  9. customdried

出典と根拠

ORDレコード
ord-e350f731bcbc4e7b9aa6480e5df2a170
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07122567B2

反応ノート

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