1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077483, compound

HRID 1359816Notes

Reaction equation

HRID 1359816 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]([C:30]([OH:32])=O)[C:25]=1[CH3:33])(=[O:12])=[O:11].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:55]1([CH2:58][NH:59][CH2:60][C@H:61]2[CH2:65][CH2:64][CH2:63][NH:62]2)[CH2:57][CH2:56]1>CN(C=O)C.O.C([O-])(O)=O.[Na+]>[CH:55]1([CH2:58][NH:59][CH2:60][C@H:61]2[CH2:65][CH2:64][CH2:63][N:62]2[C:30]([C:26]2[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]3\[C:17](=[O:22])[NH:18][C:19]4[C:15]\3=[CH:14][C:13]([S:10]([CH2:9][C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:12])=[O:11])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])=[O:32])[CH2:56][CH2:57]1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 590775075-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acidHCID 66701774HCID 66701774, compound

Product 1

HCID 59077483HCID 59077483, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (200 mg, 0.4 mmol), EDAC (150 mg, 0.78 mmol) and HOBt (54 mg, 0.4 mmol) in DMF (4 mL) was added cyclopropylmethyl-(R)-1-pyrrolidin-2-ylmethyl-amine (100 mg, 0.65 mmol) and TEA (0.12 mL). The mixture was stirred at rt for 20 hours. The reaction was diluted with water and NaHCO3, extracted with 5% methanol in DCM. The combined extracts were concentrated and purified on a silica gel column to give the titled compound.

Workup

  1. extractionextracted with 5% methanol in DCM
  2. concentrationThe combined extracts were concentrated
  3. custompurified on a silica gel column

Sources & evidence

ORD record
ord-7a2a3c45fb0342689724f3f5e1379140
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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