1-Hydroxybenzotriazole → HCID 59077710, compound

HRID 1359712Notes

Reaction equation

HRID 1359712 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:25][C:26]([CH3:32])=[CH:27][C:28]=1[C:29]([OH:31])=O)(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:55][CH2:56][CH:57]([OH:64])[CH2:58][N:59]1[CH:63]=[CH:62][N:61]=[N:60]1>CN(C=O)C>[OH:64][CH:57]([CH2:58][N:59]1[CH:63]=[CH:62][N:61]=[N:60]1)[CH2:56][NH:55][C:29]([C:28]1[CH:27]=[C:26]([CH3:32])[NH:25][C:24]=1/[CH:23]=[C:16]1\[C:17](=[O:22])[NH:18][C:19]2[C:15]\1=[CH:14][C:13]([S:10]([CH2:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])(=[O:12])=[O:11])=[CH:21][CH:20]=2)=[O:31]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 187656671-amino-3-(1H-1,2,3-triazol-1-yl)propan-2-olHCID 59077650HCID 59077650, compound

Product 1

HCID 59077710HCID 59077710, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid (100 mg, 0.2 mmol), HOBt (33 mg, 1.2 eq.), EDAC.HCl (47 mg, 1.2 eq.) and 1-amino-3-[1,2,3]triazol-1-yl-propan-2-ol (30 mg, 1.1 eq.) in DMF (2 mL) was added TEA (0.071 mL, 2.5 eq.). After stirring at rt for 2 weeks, the reaction was concentrated, diluted with DCM and several drops of methanol. After standing at rt for one hour, the resulted precipitate was collected by vacuum filtration, washed and dried to give the titled compound as a yellow solid.

Workup

  1. concentrationthe reaction was concentrated
  2. additiondiluted with DCM and several drops of methanol
  3. filtrationthe resulted precipitate was collected by vacuum filtration
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-c4f3cc68ccd14fbb90a6cd55dd36a52c
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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