1-Hydroxybenzotriazole → 5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (3-Morpholin-4-yl-propyl)-amide

HRID 1359745Notes

Reaction equation

HRID 1359745 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](O)=[O:31])[C:25]=1[CH3:33])(=[O:12])=[O:11].C1C=C[C:37]2[N:42](O)N=N[C:38]=2[CH:39]=1.CCN=C=NCCCN(C)C.Cl.[N:56]1(C(C)CN)[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1>CN(C=O)C>[N:56]1([CH2:39][CH2:38][CH2:37][NH:42][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:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])(=[O:12])=[O:11])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])=[O:31])[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 166414542-(Morpholin-4-yl)propan-1-amineHCID 590775075-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 590776315-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (3-Morpholin-4-yl-propyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (100 mg, 0.19 mmol), HOBt (31 mg, 1.2 eq.), EDAC.HCl (44 mg, 1.2 eq.) and 2-morpholin-4-yl-propylamine (69 mg, 2.5 eq.) in DMF (2 mL) was added TEA (0.066 mL, 2.5 eq.). After stirring at rt for 6 days, the reaction was concentrated, diluted with DCM, washed with sat. NaHCO3 and water, dried, concentrated and purified on a silica gel column to give the titled compound as a pale yellow solid.

Workup

  1. concentrationthe reaction was concentrated
  2. additiondiluted with DCM
  3. washwashed with sat. NaHCO3 and water
  4. customdried
  5. concentrationconcentrated
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-bc0c4869809346bcb5146aafa2f05fab
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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