5-Chloro-1H-indole-2-carboxylic acid → (+/-)-trans-N1-(tert-Butoxycarbonyl)-N2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine

HRID 546418노트

반응식

HRID 546418 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:37]([O:41][C:42]([NH:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]1[NH2:51])=[O:43])([CH3:40])([CH3:39])[CH3:38]>CN(C)C=O>[C:37]([O:41][C:42]([NH:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]1[NH:51][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:13])=[O:43])([CH3:40])([CH3:38])[CH3:39]

참가 물질

6

반응물 4

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 1514390(1R,2R)-trans-N-Boc-1,2-cyclohexanediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 68910309(+/-)-trans-N1-(tert-Butoxycarbonyl)-N2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-Chloroindole-2-carboxylic acid (2.88 g), 1-hydroxybenzotriazole monohydrate (2.08 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.95 g) were added to a solution of (±)-trans-N-tert-butoxycarbonyl-1,2-cyclohexanediamine (3.00 g) in N,N-dimethylformamide (10 ml) at room temperature. After stirring for 3 days, the reaction mixture was concentrated under reduced pressure, and dichloromethane (30 ml), a saturated aqueous solution (150 ml) of sodium hydrogencarbonate and water (150 ml) were added to the residue. After collecting colorless precipitate formed was collected by filtration and dried to obtain the title compound (5.21 g) as a colorless solid.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure, and dichloromethane (30 ml)
  2. additiona saturated aqueous solution (150 ml) of sodium hydrogencarbonate and water (150 ml) were added to the residue
  3. customAfter collecting colorless precipitate
  4. customformed
  5. filtrationwas collected by filtration
  6. customdried

출처 및 근거

ORD 기록
ord-7ae8ab8013fb4083866ea68dd66763cd
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935824B2

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