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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl((1R,2R)-2-{[(2-Chloro-6H-thieno[2,3-b]pyrrol-5-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)carbamate

HRID 1244734
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HRID 1244734 반응식
[Cl:1][C:2]1[S:9]C2CC(C(O)=O)=NC=2[CH:3]=1.[NH2:13][C@@H:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@H:15]1[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].CC[N:33]([CH:37]([CH3:39])C)[CH:34]([CH3:36])[CH3:35].C1C=CC2N([OH:49])N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:27]([O:26][C:24](=[O:25])[NH:23][C@@H:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][C@H:14]1[NH:13][C:36]([C:34]1[NH:33][C:37]2[S:9][C:2]([Cl:1])=[CH:3][C:39]=2[CH:35]=1)=[O:49])([CH3:30])([CH3:29])[CH3:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11299644tert-butyl ((1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl)carbamateHCID 219204592-Chloro-5-carboxy-6h-thieno[3,2-b]pyrrole

생성물 1

HCID 58717460
tert-Butyl((1R,2R)-2-{[(2-Chloro-6H-thieno[2,3-b]pyrrol-5-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)carbamate
수율 98.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Chloro-5-carboxy-6H-thieno[3,2-b]pyrrole (Method 4a, 5.0 g, 25.0 mmol), trans-2-amino-1-[(1,1-dimethylethoxy)carbonylamino]indan (Method 6, 6.25 g, 25.0 mmol), DIPEA (4.35 mL, 25.0 mmol) and HOBT (3.4 g, 25.0 mmol) were dissolved in DCM (200 mL) and stirred for 5 mins. EDCI (6.0 g, 31.0 mmol) was added, the reaction stirred for 24 hours and evaporated under reduced pressure. EtOAc (150 mL) was added and the mixture filtered, washed with water (2×200 mL), brine (200 mL), dried (MgSO4) and the volatiles removed by evaporation under reduced pressure to give the title compound (10.6 g, 98%) as a brown solid.

후처리

  1. stirringthe reaction stirred for 24 hours
  2. customevaporated under reduced pressure
  3. additionEtOAc (150 mL) was added
  4. filtrationthe mixture filtered
  5. washwashed with water (2×200 mL), brine (200 mL)
  6. dry with materialdried (MgSO4)
  7. customthe volatiles removed by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-34565f2e30f949f288a85958ae49d105
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07122567B2

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