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 1244727노트

반응식

HRID 1244727 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5083ec57ba6a4ee5bd0225f6761d534c
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122567B2

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