1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58742490, compound

HRID 722259Notes

Reaction equation

HRID 722259 reaction equation
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:20][O:21][CH2:22][CH2:23][C:24]([OH:26])=O.CCN=C=NCCCN(C)C.[NH2:38][C@@H:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][C@H:40]1[NH:48][C:49]([C:51]1[NH:52][C:53]2[C:58]([CH:59]=1)=[CH:57][C:56]([Cl:60])=[CH:55][CH:54]=2)=[O:50]>C(Cl)Cl>[Cl:60][C:56]1[CH:57]=[C:58]2[C:53](=[CH:54][CH:55]=1)[NH:52][C:51]([C:49]([NH:48][C@@H:40]1[CH2:41][C:42]3[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@H:39]1[NH:38][C:24](=[O:26])[CH2:23][CH2:22][O:21][CH3:20])=[O:50])=[CH:59]2

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1344423-Methoxypropionic acidHCID 58742475HCID 58742475, compound

Product 1

HCID 58742490HCID 58742490, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (180 μL, 1.05 mmol), HOBT (68 mg, 0.5 mmol), 3-methoxypropanoic acid (46 μL, 0.5 mmol) and EDAC (120 mg, 0.63 mmol) were added to a suspension of N-[(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl]-5-chloro-1H-indole-2-carboxamide (Method 5, 220 mg, 0.5 mmol) in anhydrous DCM (7 mL). The reaction was stirred at ambient temperature for approximately 16 h. The volatiles were removed by evaporation under reduced pressure, the residue dissolved in EtOAc (10 mL), washed with water (2×10 mL), brine (10 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure and the residue triturated (DCM), collected by filtration, washed with hexane (2×5 mL) and dried to give the title compound (84 mg, 41%) as a brown solid.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (10 mL)
  3. washwashed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed by evaporation under reduced pressure
  6. customthe residue triturated (DCM)
  7. filtrationcollected by filtration
  8. washwashed with hexane (2×5 mL)
  9. customdried

Sources & evidence

ORD record
ord-6d7240153aa14900bc9d23b234295d7c
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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