3-Methoxypropylamine → HCID 59077722, compound

HRID 1359731Notes

Reaction equation

HRID 1359731 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].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:56][O:57][CH2:58][CH2:59][CH2:60][NH2:61]>CN(C=O)C>[CH3:56][O:57][CH2:58][CH2:59][CH2:60][NH:61][C:30]([C:26]1[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]2\[C:17](=[O:22])[NH:18][C:19]3[C:15]\2=[CH:14][C:13]([S:10]([CH2:9][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])(=[O:12])=[O:11])=[CH:21][CH:20]=3)[NH:28][C:27]=1[CH3:29])=[O:32]

Participants

6

Reactant 4

HCID 16723-MethoxypropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 59077722HCID 59077722, compound

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 3-methoxy-propylamine (42 mg, 1.1 eq.) in DMF (2 mL) was added TEA (0.066 mL, 2.5 eq.). After stirring at rt for 10 days, the reaction was concentrated, diluted with DCM, washed with sat. NaHCO3 and water, concentrated and purified on a silica gel column to give the titled compound as a pale orange waxy solid.

Workup

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

Sources & evidence

ORD record
ord-6412b9dffce84089b99438d5412d3276
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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