1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077627, compound

HRID 1359842Notes

Reaction equation

HRID 1359842 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([OH:33])=O)[C:25]=1[CH3:34])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH:56]1[CH2:60][CH2:59][C@@H:58]([OH:61])[CH2:57]1>CN(C=O)C.C(Cl)Cl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([N:56]2[CH2:60][CH2:59][C@@H:58]([OH:61])[CH2:57]2)=[O:33])[C:25]=1[CH3:34])(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2759337(R)-3-PyrrolidinolHCID 59077497HCID 59077497, compound

Product 1

HCID 59077627HCID 59077627, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of {5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (200 mg), HOBt (1 eq.), EDAC (2 eq.), TEA (3 eq.) and (R)-pyrrolidin-3-ol (3 eq.) in DMF (4 mL) was stirred at rt for overnight. The reaction was diluted with DCM, washed with water (2×) and 10% sodium carbonate (2×). The DCM was dried, concentrated and purified on a silica gel column to give 21 mg of the titled compound. MS m/z 588 [M++1].

Workup

  1. washwashed with water (2×) and 10% sodium carbonate (2×)
  2. dry with materialThe DCM was dried
  3. concentrationconcentrated
  4. custompurified on a silica gel column

Sources & evidence

ORD record
ord-1a0861182b3744e98bf243bffb19127a
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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