1-Hydroxybenzotriazole → N-[2-(3-Acetylamino-pyrrolidin-1-yl)-ethyl]-2-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetamide

HRID 1359824Notes

Reaction equation

HRID 1359824 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.Cl.[NH2:57][CH2:58][CH2:59][N:60]1[CH2:64][CH2:63][CH:62]([NH:65][C:66](=[O:68])[CH3:67])[CH2:61]1>CN(C=O)C>[C:66]([NH:65][CH:62]1[CH2:63][CH2:64][N:60]([CH2:59][CH2:58][NH:57][C:31](=[O:33])[CH2:30][C:26]2[C:25]([CH3:34])=[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:11])=[O:12])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])[CH2:61]1)(=[O:68])[CH3:67]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23450282N-[1-(2-Amino-ethyl)-pyrrolidin-3-yl]-acetamideHCID 59077497HCID 59077497, compound

Product 1

HCID 59077664N-[2-(3-Acetylamino-pyrrolidin-1-yl)-ethyl]-2-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (260 mg, 0.5 mmol) in DMF (3 mL) was added HOBt (101 mg, 1.5 eq.), EDAC.HCl (144 mg, 3 eq.) and TEA (152 mg, 1.5 eq.). After stirring at rt for 30 mins, to the mixture was added N-[1-(2-amino-ethyl)-pyrrolidin-3-yl]-acetamide (128 mg, 1.5 eq.). After stirring at 40° C. for overnight, the cooled reaction was concentrated and the residue was purified on a silica gel column to give the title compound as a yellow solid.

Workup

  1. stirringAfter stirring at 40° C. for overnight
  2. customthe cooled reaction
  3. concentrationwas concentrated
  4. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-aa710fba45b8468d9b0fda74f948d047
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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