1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,3-Dichloro-5-(N-{(1R,2R)-1-[N-(1,1-dimethylethoxy)carbonylamino]indan-2-yl}carbamoyl)-4H-thieno[3,2-b]pyrrole

HRID 1244727ノート

反応式

HRID 1244727 の反応式
[C:1]([C:4]1[NH:8][C:7]2[C:9]([Cl:13])=[C:10]([Cl:12])[S:11][C:6]=2[CH:5]=1)([OH:3])=O.[NH2:14][C@@H:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:16]1[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:12][C:10]1[S:11][C:6]2[CH:5]=[C:4]([C:1](=[O:3])[NH:14][C@@H:15]3[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C@H:16]3[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[NH:8][C:7]=2[C:9]=1[Cl:13]

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 100143182,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxylic acidHCID 11299644tert-butyl ((1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl)carbamate

生成物 1

HCID 114199362,3-Dichloro-5-(N-{(1R,2R)-1-[N-(1,1-dimethylethoxy)carbonylamino]indan-2-yl}carbamoyl)-4H-thieno[3,2-b]pyrrole収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5-Carboxy-2,3-dichloro-4H-thieno[3,2-b]pyrrole (Method 4; 2.36 g, 10.0 mmol), trans-2-amino-1-{N-[(1,1-dimethylethoxy)]carbonylamino}indan (Method 6; 2.5 g, 10.0 mmol), DIPEA (1.7 ml, 10.0 mmol) and HOBT (1.35 g, 10.0 mmol) was stirred in DCM (75 ml) at room temperature for 2 minutes. EDCI (2.4 g, 12.5 mmol) was added and the mixture stirred at room temperature for 20 hours during which time the product precipitated. The reaction was filtered, washed with DCM (2×25 ml) and dried to give the title compound (3.7 g, 80%) as a pale green powder.

後処理

  1. customprecipitated
  2. filtrationThe reaction was filtered
  3. washwashed with DCM (2×25 ml)
  4. customdried

出典と根拠

ORDレコード
ord-5083ec57ba6a4ee5bd0225f6761d534c
出典データセット
uspto-grants-2006_10
特許番号
US07122567B2

反応ノート

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