1,2-Dichloroethane → 5-[4-(2,6-Difluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]4-methyl-1H-pyrrole-3-carboxylic Acid [3-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-2-hydroxy-propyl]-amide

HRID 1839828Notes

Reaction equation

HRID 1839828 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1/[C:11](=[CH:19]/[C:20]1[NH:24][CH:23]=[C:22]([C:25](O)=[O:26])[C:21]=1[CH3:28])/[C:12](=[O:18])[NH:13]2.[NH2:29][CH2:30][CH:31]([OH:41])[CH2:32][N:33]1[CH2:38][CH2:37][S:36](=[O:40])(=[O:39])[CH2:35][CH2:34]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C1COCC1.C(#N)C>[O:40]=[S:36]1(=[O:39])[CH2:35][CH2:34][N:33]([CH2:32][CH:31]([OH:41])[CH2:30][NH:29][C:25]([C:22]2[C:21]([CH3:28])=[C:20](/[CH:19]=[C:11]3\[C:12](=[O:18])[NH:13][C:14]4[C:10]\3=[C:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[CH:17]=[CH:16][CH:15]=4)[NH:24][CH:23]=2)=[O:26])[CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 206047681-Amino-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-propan-2-olHCID 600614295-[4-(2,6-Difluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-4-methyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 600614015-[4-(2,6-Difluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]4-methyl-1H-pyrrole-3-carboxylic Acid [3-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-2-hydroxy-propyl]-amideYield 60%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[4-(2,6-Difluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-4-methyl-1H-pyrrole-3-carboxylic acid (114 mg, 0.3 mmol) was coupled with 1-amino-3-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-propan-2-ol (1.8 mmol), HOBt (1 eq.), EDC (1.5 eq.) and TEA (3 drops) in THF (1 mL), acetonitrile (1 mL) at rt for overnight to give 102 mg (60%) of the titled compound.

Sources & evidence

ORD record
ord-e465208edda6434986068316d87b2b41
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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