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

HRID 546418Notes

Reaction equation

HRID 546418 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7ae8ab8013fb4083866ea68dd66763cd
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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